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Dayang Chem (Hangzhou) Co.,Ltd.

Dayangchem's R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. DayangChem can provide different quantities

Boc-3-Hydroxy-1-adamantyl-D-glycine

Cas:361442-00-4

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

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Sinoway Industrial Co., Ltd.

Why is SINOWAY: 1) Specialized in pharmaceutical and healthcare industrial for 34 years. 2) ISO 9001:2015 & SGS audited supplier . 3) Accept various payment terms : T.T 30-60 days. 4) We have warehouse in USA with quickly shipment . 5) We c

Top Quality 99% up Boc-3-Hydroxy-1-Adamantyl-D-Glycine / Saxagliptin Intermediate 361442-00-4

Cas:361442-00-4

Min.Order:2 Kilogram

FOB Price: $55.0 / 200.0

Type:Trading Company

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Hangzhou Dingyan Chem Co., Ltd

Items Standard Result Appearance White to off-white power White powder Solubility Soluble in meth

High purity Boc-3-Hydroxy-1-adamantyl-D-glycine CAS:361442-00-4

Cas:361442-00-4

Min.Order:1 Gram

FOB Price: $100.0 / 500.0

Type:Manufacturers

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Simagchem Corporation

Welcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our

Hebei yanxi chemical co.,LTD.

Hebei yanxi chemical co., LTD is a professional research, development and production 2-phenylacetamide enterprise backbone members by local well-known entrepreneurs and professional senior engineers in the party's "low carbon environ

Boc-3-Hydroxy-1-adamantyl-D-glycine

Cas:361442-00-4

Min.Order:100 Gram

FOB Price: $2.0

Type:Manufacturers

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Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

We can provide GMP validation service that complies with SFDA, FDA, WHO and EU EMPA.Excellent registration team could help us easlily to register our products in different countries.If you and your customer are interested in some products or need CMO

Saxagliptin intermediate manufacturer/supplier

Cas:361442-00-4

Min.Order:1 Gram

Negotiable

Type:Manufacturers

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Wuhan Fortuna Chemical Co.,Ltd

Unique advantages Guaranteed purity High quality & competitive price Quality control Fast feedback Prompt shipment Appearance:White crystalline powder Storage:cool dry place Package:1kg/foil bag;25kg/drum Application:pharmaceutical intermed

Manufacturer high quality Boc-3-Hydroxy-1-adamantyl-D-glycine Cas 361442-00-4 with good price

Cas:361442-00-4

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

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Hangzhou Think Chemical Co. Ltd

Boc-3-Hydroxy-1-adamantyl-D-glycine CAS No.:361442-00-4 Name: Boc-3-Hydroxy-1-adamantyl-D-glycine Synonyms (alphaS)-alpha-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.1(3,7)]decane-1-acetic acid Molecul

High purity Boc-3-Hydroxy-1-adamantyl-D-glycine CAS No.:361442-00-4

Cas:361442-00-4

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Other

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Henan Allgreen Chemical Co.,Ltd

he company has advanced technology, as well as a large number of excellent R & D team, to provide customers from the grams to one hundred kilograms and tons of high-quality products, competitive prices and quality se T rvice Appearance:Whit

(S)-N-tert-Butyloxycarbonyl-3-HydroxyadaMantylglycine

Cas:361442-00-4

Min.Order:1 Gram

Negotiable

Type:Manufacturers

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Ality Chemical Corporation

The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi

Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

High Quality 99% Boc-3-Hydroxy-1-adamantyl-D-glycine 361442-00-4 ISO Producer

Cas:361442-00-4

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

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SICHUAN TONGSHENG AMINOACID CO.LTD

Sichuan Tongsheng is the most strongest manufacturer and exporter of amino acids and their derivatives in China, we have the best quality and price. Guarantee high quality, competive price and reliable service. We fully compliance with ISO900

Intermediates of Saxagliptin 361442-00-4

Cas:361442-00-4

Min.Order:50 Gram

Negotiable

Type:Manufacturers

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Enke Pharma-tech Co.,Ltd. (Cangzhou, China )

Cangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-tech enterprise ,and we are dedicated to developing and manufacturing new api, intermedi

Boc-3-Hydroxy-1-adamantyl-D-glycine

Cas:361442-00-4

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Manufacturers

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Shanghai SE Pharm Co., Ltd

1. made in GMP plant, commerially 2. Normal Stock: 500kgs 3. Audit accepted. Related documents are available to offer and audited by many clients, such as Lupin, MSN, Dr reddy etc 4. Chromatographic Purity (HPLC): not less than 99

Boc-3-Hydroxy-1-adamantyl-D-glycine

Cas:361442-00-4

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

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Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

(S)-N-tert-Butoxycarbonyl-3-hydroxyadamantylglycine

Cas:361442-00-4

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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Leader Biochemical Group

About Product Details

China Largest factory Manufacturer Supply Boc-3-Hydroxy-1-adamantyl-D-glycine CAS 361442-00-4

Cas:361442-00-4

Min.Order:1 Kilogram

FOB Price: $3.0 / 10.0

Type:Lab/Research institutions

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LIDE PHARMACEUTICALS LIMITED

LIDE PHARMACEUTICALS LIMITED is a professional chemicals and APIs leading manufacturer in China. Our core business line covers APIs, Intermediates, Herb extract, etc.

(alphaS)-alpha-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Cas:361442-00-4

Min.Order:1 Kilogram

FOB Price: $0.9 / 1.0

Type:Lab/Research institutions

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Henan Tianfu Chemical Co., Ltd.

(alphaS)-alpha-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid Basic information Product Name: (alphaS)-alpha-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-hy

TIANFU-CHEM Boc-3-Hydroxy-1-adamantyl-D-glycine

Cas:361442-00-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Hebei Nengqian Chemical Import and Export Co., LTD

With our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufacturing

Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

New production CAS 361442-00-4 with best quality

Cas:361442-00-4

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Henan Sinotech Import&Export Corporation

Product Name: Boc-3-Hydroxy-1-adamantyl-D-glycine CAS No.: 361442-00-4 Molecular formula: C17H27NO5 Molecular weight: 325 Appearance: white powder Storage:Store in cool and dry place, away from

Boc-3-Hydroxy-1-adamantyl-D-glycine

Cas:361442-00-4

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Other

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Jinan Finer Chemical Co., Ltd

Product Description Product Name Boc-3-Hydroxy-1-adamantyl-D-glycine CAS No. 361442-00-4 Appearance White powder

Boc-3-Hydroxy-1-adamantyl-D-glycine

Cas:361442-00-4

Min.Order:1 Gram

FOB Price: $12.0

Type:Lab/Research institutions

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Hubei Langyou International Trading Co., Ltd

Advantages: Hubei XinRunde Chemical Co., Ltd is a renowned pharmaceutical manufacturer. We can offer high quality products at competitive price in quick delivery with 100% custom pass guaranteed. Never stop striving to offer our best serv

361442-00-4 Boc-3-Hydroxy-1-adamantyl-D-glycine

Cas:361442-00-4

Min.Order:10 Gram

Negotiable

Type:Other

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HANWAYS CHEMPHARM CO.,LIMITED

We are concentrating on APIs and pharmaceutical intermediates. With in depth knowledge and understanding in this industry, we are indulged in supplying a wide assortments of Boc-3-Hydroxy-1-adamantyl-D-glycine from Wuhan, Hube

Boc-3-Hydroxy-1-adamantyl-D-glycine

Cas:361442-00-4

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Trading Company

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Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized

Boc-3-Hydroxy-1-adamantyl-D-glycine 361442-00-4

Cas:361442-00-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Sartort Biopharma Co., Ltd

Appearance:Off-white powder Storage:ln stock Package:25kg/Barrel Transportation:Express/Sea/Air Port:Any port in china

Boc-3-Hydroxy-1-adamantyl-D-glycine

Cas:361442-00-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Huarong Pharm Co., Ltd.

Hangzhou Huarong Pharm Co., Ltd. established since 2009 , has been always focusing on supplying products and services to our clients in the field of small molecule drug. Huarong Pharm has built platforms for the research, development and manufac

(alphaS)-alpha-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Cas:361442-00-4

Min.Order:1 Gram

FOB Price: $1.0 / 2.0

Type:Lab/Research institutions

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Wuhan Han Sheng New Material Technology Co.,Ltd

Our Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We

Factory Supply High Quality CAS 361442-00-4 (S)-N-tert-Butyloxycarbonyl-3-HydroxyadaMantylglycine

Cas:361442-00-4

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

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Qingdao Beluga Import and Export Co., LTD

Boc-3-Hydroxy-1-adamantyl-D-glycine CAS:361442-00-4 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high qua

Boc-3-Hydroxy-1-adamantyl-D-glycine CAS:361442-00-4

Cas:361442-00-4

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

Boc-3-Hydroxy-1-adamantyl-D-glycine

Cas:361442-00-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine ethyl ester

N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine ethyl ester

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 18 - 65℃; for 2h;98.1%
(αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃; for 12h;98%
With potassium phosphate In tetrahydrofuran; sodium hydroxide at 20℃; for 2h;88%
Stage #1: (αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid; di-tert-butyl dicarbonate With sodium hydroxide for 4h; pH=10;
Stage #2: With sulfuric acid In Isopropyl acetate; water for 0.0833333 - 0.166667h; pH=2.0 - 8;
88%
N-tert-butoxycarbonyl-3-hydroxy-1-adamantaneglycine

N-tert-butoxycarbonyl-3-hydroxy-1-adamantaneglycine

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With (1R,2S)-2-Amino-1,2-diphenylethanol In ethyl acetate at 20℃; for 2h; Reflux; Resolution of racemate;56%
Multi-step reaction with 2 steps
1: ethyl acetate / 17.42 h / 20 - 70 °C / Resolution of racemate
2: hydrogenchloride / ethyl acetate; water / pH 3
View Scheme
Multi-step reaction with 2 steps
1: ethanol / 0.08 h / Resolution of racemate; Reflux
2: hydrogenchloride / water; ethyl acetate / pH 2
View Scheme
(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid
361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

A

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

B

(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid
681282-72-4

(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid

Conditions
ConditionsYield
With potassium hydroxide; potassium permanganate at 60 - 90℃; for 1.5h;A 51%
B 17%
With potassium hydroxide; potassium permanganate In water at 60 - 90℃; for 1.5h;A 51%
B 17%
(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid
361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With potassium permanganate; water; potassium hydroxide at 60 - 90℃; for 1.5h;51%
With potassium permanganate; potassium hydroxide at 90℃;49%
With potassium permanganate; tetrabutylammomium bromide; potassium hydroxide In water at 20 - 25℃;18.6 g
(S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile
361441-95-4

(S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
2: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
3: 4.07 g / K2CO3 / dimethylformamide / 19 h
4: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride; water / acetic acid / 80 °C
2: hydrogen; palladium 10% on activated carbon / acetic acid
3: triethylamine / methanol
4: potassium permanganate; potassium hydroxide / 90 °C
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
2.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
3.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
3.2: 0 - 5 °C
4.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride; water / acetic acid / 18 h / 80 °C
2: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
3: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
4: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme
(R)-N-((S)-(adamantan-1-yl)(carboxy)methyl)-2-hydroxy-1-phenylethan-1-ammonium chloride

(R)-N-((S)-(adamantan-1-yl)(carboxy)methyl)-2-hydroxy-1-phenylethan-1-ammonium chloride

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
2: 4.07 g / K2CO3 / dimethylformamide / 19 h
3: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogen; palladium 10% on activated carbon / acetic acid
2: triethylamine / methanol
3: potassium permanganate; potassium hydroxide / 90 °C
View Scheme
Multi-step reaction with 3 steps
1.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
2.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
2.2: 0 - 5 °C
3.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
2: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
3: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme
1-adamantanemethanol
770-71-8

1-adamantanemethanol

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C
2: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating
3: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
4: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
5: 4.07 g / K2CO3 / dimethylformamide / 19 h
6: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 6 steps
1.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C
1.2: 0 - 5 °C
2.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C
3.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
4.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
5.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
5.2: 0 - 5 °C
6.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 6 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
1.2: 0.5 h / -78 °C / Inert atmosphere
2.1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux
3.1: hydrogenchloride; water / acetic acid / 18 h / 80 °C
4.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
5.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
6.1: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 7 steps
1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium bromide / dichloromethane; water / 12 h / 5 - 30 °C
2.1: sodium hydrogen sulfate / water; methanol / 5 - 77 °C
3.1: sulfuric acid / 45 - 50 °C
3.2: 2 h / 20 - 35 °C
4.1: 10 wt% Pd(OH)2 on carbon; acetic acid; hydrogen / methanol / 760.05 Torr
5.1: sulfuric acid / 110 - 112 °C
6.1: sulfuric acid; nitric acid / 10 - 25 °C
7.1: sodium hydroxide / 5 h / 25 - 30 °C
View Scheme
1-Adamantanecarboxylic acid
828-51-3

1-Adamantanecarboxylic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 100 percent / diethyl ether; hexane; methanol / 3 h / 20 °C
2: 96 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C
3: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C
4: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating
5: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
6: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
7: 4.07 g / K2CO3 / dimethylformamide / 19 h
8: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 8 steps
1.1: thionyl chloride / 3 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
3.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C
3.2: 0 - 5 °C
4.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C
5.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
6.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
7.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
7.2: 0 - 5 °C
8.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 8 steps
1.1: thionyl chloride / 4 h / Reflux
2.1: sodium / Petroleum ether / 20 °C
2.2: 20 °C
2.3: 6 h / Reflux
3.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / water; tert-butyl alcohol / 3 h / 40 - 45 °C
4.1: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h
5.1: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C
6.1: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10
7.1: potassium permanganate; potassium hydroxide / 2 h / 90 °C
8.1: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate
View Scheme
1-Adamantanecarbaldehyde
2094-74-8

1-Adamantanecarbaldehyde

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating
2: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
3: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
4: 4.07 g / K2CO3 / dimethylformamide / 19 h
5: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 5 steps
1: sodium hydrogensulfite / 0 - 60 °C
2: hydrogenchloride; water / acetic acid / 80 °C
3: hydrogen; palladium 10% on activated carbon / acetic acid
4: triethylamine / methanol
5: potassium permanganate; potassium hydroxide / 90 °C
View Scheme
Multi-step reaction with 5 steps
1.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C
2.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
3.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
4.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
4.2: 0 - 5 °C
5.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 5 steps
1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux
2: hydrogenchloride; water / acetic acid / 18 h / 80 °C
3: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
4: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
5: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydrogen sulfate / water; methanol / 5 - 77 °C
2.1: sulfuric acid / 45 - 50 °C
2.2: 2 h / 20 - 35 °C
3.1: 10 wt% Pd(OH)2 on carbon; acetic acid; hydrogen / methanol / 760.05 Torr
4.1: sulfuric acid / 110 - 112 °C
5.1: sulfuric acid; nitric acid / 10 - 25 °C
6.1: sodium hydroxide / 5 h / 25 - 30 °C
View Scheme
methyl adamantane-1-carboxylate
711-01-3

methyl adamantane-1-carboxylate

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 96 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C
2: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C
3: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating
4: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
5: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
6: 4.07 g / K2CO3 / dimethylformamide / 19 h
7: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 7 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C
2.2: 0 - 5 °C
3.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C
4.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
5.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
6.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
6.2: 0 - 5 °C
7.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 7 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
2.2: 0.5 h / -78 °C / Inert atmosphere
3.1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux
4.1: hydrogenchloride; water / acetic acid / 18 h / 80 °C
5.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
6.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
7.1: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme
(S)-(+)-β-amino-1-adamantaneacetic acid
95853-35-3

(S)-(+)-β-amino-1-adamantaneacetic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4.07 g / K2CO3 / dimethylformamide / 19 h
2: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid; nitric acid / 10 - 25 °C
2: sodium hydroxide / 5 h / 25 - 30 °C
View Scheme
(αS)-α-[(1,1-dimethylethoxy)carbonyl]amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(αS)-α-[(1,1-dimethylethoxy)carbonyl]amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With hydrogenchloride In water; ethyl acetate pH=3;
N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine
1334321-39-9

N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine; isobutyl chloroformate / tetrahydrofuran / 1.5 h / -8 °C
1.2: 18 h / -8 - 25 °C
2.1: ethyl acetate / 17.42 h / 20 - 70 °C / Resolution of racemate
3.1: hydrogenchloride / ethyl acetate; water / pH 3
View Scheme
Multi-step reaction with 3 steps
1.1: dicyclohexyl-carbodiimide / dimethyl sulfoxide / 5 h / 20 °C
1.2: 53 h / 20 - 50 °C
1.3: 2 h
2.1: ethanol / 0.08 h / Resolution of racemate; Reflux
3.1: hydrogenchloride / water; ethyl acetate / pH 2
View Scheme
(S)-(+)-(adamant-1-yl)aminoacetic acid hydrochloride
102502-64-7

(S)-(+)-(adamant-1-yl)aminoacetic acid hydrochloride

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / methanol
2: potassium permanganate; potassium hydroxide / 90 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
2: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme
2-(adamantan-1-yl)-2-aminoacetic acid
59768-71-7, 60256-21-5, 95853-35-3, 100926-41-8

2-(adamantan-1-yl)-2-aminoacetic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10
2: potassium permanganate; potassium hydroxide / 2 h / 90 °C
3: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate
View Scheme
1-acetyladamantane
1660-04-4

1-acetyladamantane

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / water; tert-butyl alcohol / 3 h / 40 - 45 °C
2: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h
3: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C
4: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10
5: potassium permanganate; potassium hydroxide / 2 h / 90 °C
6: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate
View Scheme
oxo-tricyclo[3.3.1.13,7]decan-1-yl-acetic acid
16091-98-8

oxo-tricyclo[3.3.1.13,7]decan-1-yl-acetic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h
2: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C
3: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10
4: potassium permanganate; potassium hydroxide / 2 h / 90 °C
5: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate
View Scheme
1-adamantyl-2-hydroxyiminoacetic acid
16091-97-7

1-adamantyl-2-hydroxyiminoacetic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C
2: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10
3: potassium permanganate; potassium hydroxide / 2 h / 90 °C
4: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate
View Scheme
1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sodium / Petroleum ether / 20 °C
1.2: 20 °C
1.3: 6 h / Reflux
2.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / water; tert-butyl alcohol / 3 h / 40 - 45 °C
3.1: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h
4.1: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C
5.1: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10
6.1: potassium permanganate; potassium hydroxide / 2 h / 90 °C
7.1: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate
View Scheme
3-hydroxytricyclo[3.3.1.13'7]decane-1-carbaldehyde

3-hydroxytricyclo[3.3.1.13'7]decane-1-carbaldehyde

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C
2.1: water / 0.17 h / 0 - 2 °C
2.2: 14.5 h / -4 - 80 °C
3.1: hydrogenchloride; water / 1 h / 24 - 80 °C
3.2: 12 h / 80 - 82 °C
4.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr
5.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C
5.2: 2.08 h / 3 - 26 °C
5.3: 12 h / 40 °C
View Scheme
C11H17O5S(1-)*Na(1+)

C11H17O5S(1-)*Na(1+)

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: water / 0.17 h / 0 - 2 °C
1.2: 14.5 h / -4 - 80 °C
2.1: hydrogenchloride; water / 1 h / 24 - 80 °C
2.2: 12 h / 80 - 82 °C
3.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr
4.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C
4.2: 2.08 h / 3 - 26 °C
4.3: 12 h / 40 °C
View Scheme
(2S)-[((1S)-2-hydroxy-1-phenylethyl)amino]-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)ethanenitrile

(2S)-[((1S)-2-hydroxy-1-phenylethyl)amino]-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)ethanenitrile

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; water / 1 h / 24 - 80 °C
1.2: 12 h / 80 - 82 °C
2.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr
3.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C
3.2: 2.08 h / 3 - 26 °C
3.3: 12 h / 40 °C
View Scheme
(2S)-[3-chlorotricyclo[3.3.1.13'7]dec-1-yl]-[((1S)-2-hydroxy-1-phenylethyl)amino]ethanoic acid hydrochloride

(2S)-[3-chlorotricyclo[3.3.1.13'7]dec-1-yl]-[((1S)-2-hydroxy-1-phenylethyl)amino]ethanoic acid hydrochloride

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr
2.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C
2.2: 2.08 h / 3 - 26 °C
2.3: 12 h / 40 °C
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(2S)-amino[3-chlorotricyclo[3.3.1.13'7]dec-1-yl]ethanoic acid hydrochloride

(2S)-amino[3-chlorotricyclo[3.3.1.13'7]dec-1-yl]ethanoic acid hydrochloride

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Stage #1: (2S)-amino[3-chlorotricyclo[3.3.1.13'7]dec-1-yl]ethanoic acid hydrochloride With water; potassium carbonate In tetrahydrofuran at 3 - 10℃; for 0.166667h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 3 - 26℃; for 2.08333h;
Stage #3: With water at 40℃; for 12h;
1.16 g
3-hydroxyadamantane-1-carboxylic acid
42711-75-1

3-hydroxyadamantane-1-carboxylic acid

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sodium tetrahydroborate / tetrahydrofuran / 2.5 h / 0 - 31 °C
1.2: 14.5 h / 0 - 30 °C
1.3: 1 h / 0 - 10 °C
2.1: potassium bromide; sodium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane; water / 0 - 5 °C
3.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C
4.1: water / 0.17 h / 0 - 2 °C
4.2: 14.5 h / -4 - 80 °C
5.1: hydrogenchloride; water / 1 h / 24 - 80 °C
5.2: 12 h / 80 - 82 °C
6.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr
7.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C
7.2: 2.08 h / 3 - 26 °C
7.3: 12 h / 40 °C
View Scheme
1-hydroxy-3-hydroxymethyladamantane
38584-37-1

1-hydroxy-3-hydroxymethyladamantane

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium bromide; sodium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane; water / 0 - 5 °C
2.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C
3.1: water / 0.17 h / 0 - 2 °C
3.2: 14.5 h / -4 - 80 °C
4.1: hydrogenchloride; water / 1 h / 24 - 80 °C
4.2: 12 h / 80 - 82 °C
5.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr
6.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C
6.2: 2.08 h / 3 - 26 °C
6.3: 12 h / 40 °C
View Scheme
1-acetyl-3-chloroadamantane
143467-20-3

1-acetyl-3-chloroadamantane

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: potassium hydroxide / water / 6 h / Reflux
2: potassium hydroxide; potassium permanganate / water; tert-butyl alcohol / 4.5 h / 35 - 45 °C
3: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h / 0 - 5 °C / pH 7
4: sodium hydroxide; nickel-aluminum alloy / water / 50 °C
5: hydrogenchloride / water; tetrahydrofuran / 12 h / 20 °C / pH 10
6: ethanol / 0.08 h / Resolution of racemate; Reflux
7: hydrogenchloride / water; ethyl acetate / pH 2
View Scheme
C12H18NO3(1-)*Na(1+)

C12H18NO3(1-)*Na(1+)

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water; tetrahydrofuran / 12 h / 20 °C / pH 10
2: ethanol / 0.08 h / Resolution of racemate; Reflux
3: hydrogenchloride / water; ethyl acetate / pH 2
View Scheme
C17H27NO5*C20H24N2O2

C17H27NO5*C20H24N2O2

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With hydrogenchloride In water; ethyl acetate pH=2;0.96 g
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid
709031-45-8

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid

tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate
361442-01-5

tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile Solvent; Large scale;98.1%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h;46%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

cis-2-azabicyclo[3.1.0]hexane hydrochloride
841302-41-8

cis-2-azabicyclo[3.1.0]hexane hydrochloride

(2S,3R)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine
841302-42-9

(2S,3R)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dichloromethane at 20℃; for 20h;97.5%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

bis(pentafluorophenyl)carbonate
59483-84-0

bis(pentafluorophenyl)carbonate

pentafluorophenyl (2S)-2-((t-butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetate

pentafluorophenyl (2S)-2-((t-butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetate

Conditions
ConditionsYield
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid With triethylamine In ethyl acetate at 25℃; for 0.666667h;
Stage #2: bis(pentafluorophenyl)carbonate In ethyl acetate at 25℃; for 2h;
93.1%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

D-cis-4,5-methanoprolineamide methanesulfonic acid salt
1312338-82-1

D-cis-4,5-methanoprolineamide methanesulfonic acid salt

(S)-N-Boc-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinamide
1564266-87-0

(S)-N-Boc-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h;93%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

2,2'-dipyridyl carbonate
1659-31-0

2,2'-dipyridyl carbonate

2-pyridyl (2S)-2-((t-butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetate

2-pyridyl (2S)-2-((t-butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetate

Conditions
ConditionsYield
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid With triethylamine In ethyl acetate at 25℃; for 0.666667h;
Stage #2: 2,2'-dipyridyl carbonate In ethyl acetate at 25℃; for 3h;
92.2%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(1S)-α-amino-3-hydroxyadamantane-acetic acid hydrochloride
865999-64-0

(1S)-α-amino-3-hydroxyadamantane-acetic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane; isopropyl alcohol at 10 - 35℃; for 8h;90%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

bis-(p-nitrophenyl) carbonate
5070-13-3

bis-(p-nitrophenyl) carbonate

4-nitrophenyl (2S)-2-((t-butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetate

4-nitrophenyl (2S)-2-((t-butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetate

Conditions
ConditionsYield
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid With dmap; triethylamine In N,N-dimethyl-formamide at 25℃; for 0.666667h;
Stage #2: bis-(p-nitrophenyl) carbonate In N,N-dimethyl-formamide at 70℃; for 5h; Solvent;
90%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

(S)-N-boc-(3-hydroxyadamantan-1-yl)glycine succinimide ester

(S)-N-boc-(3-hydroxyadamantan-1-yl)glycine succinimide ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 25℃; for 1h;90%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide

tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate
361442-01-5

tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate

Conditions
ConditionsYield
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid; (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide With N-ethyl-N,N-diisopropylamine In ethyl acetate at 0℃; for 0.5h;
Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 0 - 20℃; for 4.5h;
89.3%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(2S,4S,5S)-4,5-methano-L-proline carboxylamide trifluoroacetate

(2S,4S,5S)-4,5-methano-L-proline carboxylamide trifluoroacetate

tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate
361442-01-5

tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate

Conditions
ConditionsYield
With TEA; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;85%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;85%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

1,4-diaza-bicyclo[2.2.2]octane
280-57-9

1,4-diaza-bicyclo[2.2.2]octane

(<αS)-<α[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.137] decane-1-acetic acid DABCO salt
709031-42-5

(<αS)-<α[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.137] decane-1-acetic acid DABCO salt

Conditions
ConditionsYield
In Isopropyl acetate; water; ethyl acetate at 20℃;79%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

L-trans-4,5-methanoprolineamide methanesulfonic acid salt
1564266-70-1

L-trans-4,5-methanoprolineamide methanesulfonic acid salt

(S)-N-Boc-3-hydroxyadamantylglycine-L-trans-4,5-methanoprolinamide

(S)-N-Boc-3-hydroxyadamantylglycine-L-trans-4,5-methanoprolinamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h;79%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

D-trans-4,5-methanoprolineamide methanesulfonic acid salt
1564266-74-5

D-trans-4,5-methanoprolineamide methanesulfonic acid salt

(S)-N-Boc-3-hydroxyadamantylglycine-D-trans-4,5-methanoprolinamide
1564267-02-2

(S)-N-Boc-3-hydroxyadamantylglycine-D-trans-4,5-methanoprolinamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h;71%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(1RS,5SR)-2-azabicyclo[3.1.0]hexane hydrochloride
841302-37-2

(1RS,5SR)-2-azabicyclo[3.1.0]hexane hydrochloride

A

(2R,3S)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine
841302-55-4

(2R,3S)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine

B

(2S,3R)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine
841302-42-9

(2S,3R)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dichloromethane at 20℃; for 20h;A 27.4%
B 40.6%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid
681282-72-4

(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid

Conditions
ConditionsYield
With potassium permanganate; potassium hydroxide In water at 60 - 85℃; for 1.5h;25%
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

N-(cyanomethyl)ethylamine
24426-40-2

N-(cyanomethyl)ethylamine

[(cyanomethyl-ethyl-carbamoyl)-(3-hydroxy-adamantan-1-yl)-methyl]-carbamic acid tert-butyl ester

[(cyanomethyl-ethyl-carbamoyl)-(3-hydroxy-adamantan-1-yl)-methyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(methylamino)acetonitrile
5616-32-0

(methylamino)acetonitrile

[(cyanomethyl-methyl-carbamoyl)-(3-hydroxy-adamantan-1-yl)-methyl]-carbamic acid tert-butyl ester

[(cyanomethyl-methyl-carbamoyl)-(3-hydroxy-adamantan-1-yl)-methyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

2-amino-N-cyanomethyl-2-(3-hydroxy-adamantan-1-yl)-N-methyl-acetamide

2-amino-N-cyanomethyl-2-(3-hydroxy-adamantan-1-yl)-N-methyl-acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: EDAC; HOAt; Et3N / CH2Cl2
2: TFA / CH2Cl2
View Scheme
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

2-amino-N-cyanomethyl-N-ethyl-2-(3-hydroxy-adamantan-1-yl)-acetamide

2-amino-N-cyanomethyl-N-ethyl-2-(3-hydroxy-adamantan-1-yl)-acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: EDAC; HOAt; Et3N / CH2Cl2
2: TFA / CH2Cl2
View Scheme
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

[(S)-2-((1S,3S,5S)-3-Cyano-2-aza-bicyclo[3.1.0]hex-2-yl)-1-(3-fluoro-adamantan-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

[(S)-2-((1S,3S,5S)-3-Cyano-2-aza-bicyclo[3.1.0]hex-2-yl)-1-(3-fluoro-adamantan-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C
2: 94 percent / diethylaminosulfur trifluoride / CH2Cl2 / 0.25 h / -78 °C
3: 82 percent / imidazole; pyridine; POCl3 / -20 °C
View Scheme
Multi-step reaction with 3 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C
2: diethylamino-sulfur trifluoride / dichloromethane / 0.25 h / -78 °C / Inert atmosphere
3: 1H-imidazole; pyridine; trichlorophosphate / 0.67 h / -30 °C / Inert atmosphere
View Scheme
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester
709031-43-6

3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C
2.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h
2.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 17.5 h / 0 °C / Inert atmosphere
2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C
2.2: 20 - 25 °C / pH > 10
View Scheme
Multi-step reaction with 2 steps
1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
2.2: 18 h / 20 °C
View Scheme
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(S)-N-Boc-3-fluoroadamantylglycine-L-cis-4,5-methanoprolinamide
361442-06-0

(S)-N-Boc-3-fluoroadamantylglycine-L-cis-4,5-methanoprolinamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C
2: 94 percent / diethylaminosulfur trifluoride / CH2Cl2 / 0.25 h / -78 °C
View Scheme
Multi-step reaction with 2 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C
2: diethylamino-sulfur trifluoride / dichloromethane / 0.25 h / -78 °C / Inert atmosphere
View Scheme
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(S)-3-fluoroadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt

(S)-3-fluoroadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C
2: 94 percent / diethylaminosulfur trifluoride / CH2Cl2 / 0.25 h / -78 °C
3: 72 percent / CH2Cl2 / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C
2: diethylamino-sulfur trifluoride / dichloromethane / 0.25 h / -78 °C / Inert atmosphere
3: 1H-imidazole; pyridine; trichlorophosphate / 0.67 h / -30 °C / Inert atmosphere
4: dichloromethane / 0.5 h / 20 °C
View Scheme
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

(S)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt
361442-05-9

(S)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C
2.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h
2.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C
3.1: 95 percent / CH2Cl2 / 2.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: benzotriazol-1-ol / dichloromethane / 0.08 h / -5 - 0 °C
1.2: 15.5 h / -7 - 10 °C
2.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 6.33 h / -3 - 15 °C
2.2: 7 - 15 °C / pH 10 - 10.5
3.1: dichloromethane / -5 - 2 °C
View Scheme
Multi-step reaction with 4 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / -78 - 0 °C / Inert atmosphere
3: 1H-imidazole; pyridine; trichlorophosphate / 0.75 h / -30 °C / Inert atmosphere
4: water / dichloromethane / 1.5 h / 0 °C
View Scheme

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