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COLORCOM LTD.

Colorcom is a global leader in industrial chemical manufacturing and is continuously innovating and transforming to exceed client expectations and industry standards. Colorcom prides itself on superior customer and technical focus, while focusing on

(S)-Tert-Butyl 2-Carbamoyl-2, 3-Dihydro-1H-Pyrrole-1-Carboxylate

Cas:709031-38-9

Min.Order:1 Metric Ton

Negotiable

Type:Manufacturers

inquiry

Dayang Chem (Hangzhou) Co.,Ltd.

As a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem’s R&D center offer custom synthesis according to the contract research and development services for the fine chemicals, ph

(2S)-2-(Aminocarbonyl)-2,3-dihydro-1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Xiamen Hisunny Chemical Co.,Ltd

Best quality & Attractive price & Professional service; Trial & Pilot & Commercial Hisunny Chemical is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality intermediates, specia

(S)-Boc-2-carbamoyl-2,3-dihydro-1H-pyrrole

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Shanghai Hope Chem Co., Ltd

1. Product advantages: exquisite appearance and unique functions. 2. Product Advantages: Our products are the best,fast speed ,in large stock 3. High-quality products and thoughtful service are your greatest satisfaction. 4. The product

(S)-tert-Butyl 2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

TaiChem Taizhou Limited

Established in May 2015, TaiChem Ltd. is initially invested by a British research and development company and started by PhDs back from aboard. The company is registered in China Medical City (CMC), Taizhou, Jiangsu Province, and the production site

(S)-tert-Butyl?2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate

Cas:709031-38-9

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Xiamen Jenny Chemical Technology Co., Ltd.

GMP standard, high purity, competitive price, in stock 1. Quick Response: within 6 hours after receiving your email. 2. Quality Guarantee: All products are strictly tested by our QC, confirmed by QA, and approved by a third-party lab in China, USA,

1H-Pyrrole-1-carboxylicacid,2-(aMinocarbonyl)-2,3-dihydro-,1,1-diMethylethylester,(2S)-

Cas:709031-38-9

Min.Order:1 Milligram

Negotiable

Type:Trading Company

inquiry

TAIZHOU ZHENYU BIOTECHNOLOGY CO., LTD

Zhenyu biotech exported this product to many countries and regions at best price. if you are looking for the material's manufacturer or supplier in china, zhenyu biotech is your best choice. pls contact with us freely for getting detailed

1H-Pyrrole-1-carboxylic acid, 2-(aMinocarbonyl)-2,3-dihydro-, 1,1-diMethylethyl ester, (2S)-

Cas:709031-38-9

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Lab/Research institutions

inquiry

Bluecrystal chem-union

We are a Union of chemistry in China, consists of chemists,engineers, laboratories,factories in China. We organize surplus capacity of R&D and production as well as custom synthesis for chemical products and chemical business project. We are supp

1H-Pyrrole-1-carboxylic acid, 2-(aminocarbonyl)-2,3-dihydro-,1,1-dimethylethyl ester, (2S)-

Cas:709031-38-9

Min.Order:1 Metric Ton

FOB Price: $1.0

Type:Trading Company

inquiry

Hangzhou Dingyan Chem Co., Ltd

Enterprise standard Application:Saxagliptin Intermediate

(S)-Boc-2-carbamoyl-2,3-dihydro-1H-pyrrole

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Antimex Chemical Limied

Our own factory produces direct sales with absolute price advantage Application:Pharmaceutical industry Transportation:By sea Port:Shanghai/tianjin

1H-Pyrrole-1-carboxylic acid, 2-(aminocarbonyl)-2,3-dihydro-,1,1-dimethylethyl ester, (2S)-

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Fandachem Co.,Ltd

(S)-Boc-2-carbamoyl-2,3-dihydro-1H-pyrroleAppearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:pharmaceutical intermediate Transportation:by air, by sea, by express

(S)-Boc-2-carbamoyl-2,3-dihydro-1H-pyrrole

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Other

inquiry

Hunan Longxianng Runhui Trading Co.,Ltd

R & D enterprises have their own stock in stockAppearance:To be subject to the object Package:Customized Application:pharmaceutical intermediates Transportation:Air Port:Shanghai;Guangzhou

(S)-Boc-2-carbamoyl-2,3-dihydro-1H-pyrrole

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

ZHEJIANG JIUZHOU CHEM CO.,LTD

factory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin

Amadis Chemical Co., Ltd.

1.Professional synthesis laboratory and production base. 2.Strong synthesis team and service team. 3.Professional data management system. 4.We provide the professional test date and product information ,ex. HNMR ,CNMR,FNMR, HPLC/G

(S)-tert-Butyl 2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate

Cas:709031-38-9

Min.Order:10 Milligram

Negotiable

Type:Lab/Research institutions

inquiry

Shanghai Hanhong Scientific Co.,Ltd.

factory,reasonable price Appearance:detailed see specifications Storage:Store in dry, dark and ventilated place. Package:according to the clients requirement Application:pharmaceutical intermediates Transportation:by courier,air or sea Port:S

(S)-tert-Butyl 2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate709031-38-9

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Nanjing Norris Pharm Technology Co., Ltd.

R & D enterprises have their own stock in stockAppearance:To be subject to the object Package:Customized Application:pharmaceutical intermediates Transportation:Air Port:Shanghai;Guangzhou

(S)-Boc-2-carbamoyl-2,3-dihydro-1H-pyrrole

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Haiqiang Chemical Co.,Ltd.

Enterprise standard Application:Saxagliptin Intermediate

(S)-Boc-2-carbamoyl-2,3-dihydro-1H-pyrrole

Cas:709031-38-9

Min.Order:0 Metric Ton

Negotiable

Type:Other

inquiry

ENAO Chemical Co, Limited

kodgyq8oAppearance:white powders Storage:Store at 2-8°C. Package:As per buyer requirement Application:Pharmaceuticals, Skincare, Medical Ingedients and others Transportation:By courier or By sea Port:As per buyer requirement

(S)-tert-Butyl 2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Skyrun Industrial Co.,Ltd

Adequate stocks available,prompt shipment,Strictly control on quality,Timely after-sales Application:Intermediate

(S)-tert-butyl 2-carbamoyl-2,3-dihydropyrrole-1-carboxylate

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Topbatt Chemical Co., Ltd.

Topbatt Chemical Co., Ltd., Established in 2019, located in Shenzhen, Guangdong Province, is a Manufacturer and Trading company which specialized in fine chemicals like Pharmaceutical Reference Standards and Stable Isotopes. Our Stable Isotopes produ

Saxagliptin Impurity 12

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

coolpharm Ltd

Known for its best quality and competitve price, this chemicals we offered is widely appreciated by our customers.Appearance:yellow to white solid Storage:keep sealed and keep from direct light Package:According client's requirements Application:Phar

(S)-TERT-BUTYL 2-CARBAMOYL-2,3-DIHYDRO-1H-PYRROLE-1-CARBOXYLATE

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Other

inquiry

Shenzhen Sumshine Biotech Co., Ltd.

1. Our staff are all biomedical related majors with rich experience in the pharmaceutical industry, and can provide you with more professional services.2. Our supplier has a good quality management system, and the quality of products is reliable and

Saxagliptin Impurity 12

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Beyond Pharmaceutical Co., Ltd

(S)-Boc-2-carbamoyl-2,3-dihydro-1H-pyrrole

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

NovaChemistry

High purity Application:Pharmaceutical intermediates, Material synthesis and analyzing the expectant ingredients

Saxagliptin Impurity 12

Cas:709031-38-9

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Synthetic route

(5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester
178172-26-4

(5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
With sodium isopropylate; formamide In diethyl ether at 20℃; for 2.16667h; Solvent; Temperature; Cooling with ice;93%
With Candida antarctica lipase B; ammonium carbamate; Ascarite; calcium chloride at 50℃; for 72h; Product distribution; Kinetics; Further Variations:; Reagents; Temperatures;81%
Multi-step reaction with 2 steps
1: water; lithium hydroxide / ethanol
2: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
View Scheme
N-BOC dehydroproline DIPEA

N-BOC dehydroproline DIPEA

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Stage #1: N-BOC dehydroproline DIPEA With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -25 - -20℃; for 2h;
Stage #2: With ammonia In tetrahydrofuran at 0 - 20℃; for 3h;
90%
(S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid diisopropylethylamine salt
709031-37-8

(S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid diisopropylethylamine salt

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Stage #1: (S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid diisopropylethylamine salt With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -20 - 0℃; for 3h;
Stage #2: With ammonium carbonate In tetrahydrofuran at 0 - 20℃;
90%
With ammonia; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran1.5 g
1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid
90104-21-5

1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Stage #1: 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -25 - -20℃; for 2h; Large scale;
Stage #2: With ammonia In tetrahydrofuran at 0 - 20℃; for 3h; Large scale;
90%
With 4-methyl-morpholine; ammonia; methanesulfonyl chloride at -15 - -8℃;359.7 g
4,5-dihydro-1H-pyrrole-1,5-dicarboxylic acid 1-(1,1-dimethylethyl) sodium salt

4,5-dihydro-1H-pyrrole-1,5-dicarboxylic acid 1-(1,1-dimethylethyl) sodium salt

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride
3945-69-5

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

A

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

B

4, 6-DIMEO-1, 3,5-triazene ether (DMT-ether)

4, 6-DIMEO-1, 3,5-triazene ether (DMT-ether)

Conditions
ConditionsYield
With sodium hydroxide; sodium dihydrogenphosphate; ammonium chloride at 20℃; for 4h; pH=6.20; Conversion of starting material;A 87%
B 12%
(5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester
178172-26-4

(5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester

A

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

B

(R)-tert-butyl 2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate

(R)-tert-butyl 2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate

Conditions
ConditionsYield
With sodium methylate; formamide In methanol at 20℃; for 4.5h;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: dmap
2: lithium triethylborohydride / toluene / -70 - -60 °C
3: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
4: water; lithium hydroxide / ethanol
5: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
View Scheme
Multi-step reaction with 4 steps
1.1: dmap / toluene / 3 h / 25 °C / Large scale
2.1: lithium triethylborohydride / toluene; tetrahydrofuran / 0.5 h / -45 °C / Large scale
2.2: 3 h / 25 °C / Large scale
3.1: lithium hydroxide monohydrate / water; ethanol / 2 h / 25 °C / Large scale
4.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -25 - -20 °C / Large scale
4.2: 3 h / 0 - 20 °C / Large scale
View Scheme
5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester
194594-23-5

5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
2: water; lithium hydroxide / ethanol
3: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
View Scheme
(S)-ethyl N-tert-butoxycarbonylpyroglutamate
144978-35-8, 144978-12-1

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lithium triethylborohydride / toluene / -70 - -60 °C
2: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
3: water; lithium hydroxide / ethanol
4: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
View Scheme
Multi-step reaction with 3 steps
1.1: lithium triethylborohydride / toluene; tetrahydrofuran / 0.5 h / -45 °C / Large scale
1.2: 3 h / 25 °C / Large scale
2.1: lithium hydroxide monohydrate / water; ethanol / 2 h / 25 °C / Large scale
3.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -25 - -20 °C / Large scale
3.2: 3 h / 0 - 20 °C / Large scale
View Scheme
ethyl (S)-pyroglutamate
7149-65-7

ethyl (S)-pyroglutamate

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: dmap
2: lithium triethylborohydride / toluene / -70 - -60 °C
3: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
4: water; lithium hydroxide / ethanol
5: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
View Scheme
Multi-step reaction with 4 steps
1.1: dmap / toluene / 3 h / 25 °C / Large scale
2.1: lithium triethylborohydride / toluene; tetrahydrofuran / 0.5 h / -45 °C / Large scale
2.2: 3 h / 25 °C / Large scale
3.1: lithium hydroxide monohydrate / water; ethanol / 2 h / 25 °C / Large scale
4.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -25 - -20 °C / Large scale
4.2: 3 h / 0 - 20 °C / Large scale
View Scheme
4,5-duhydro-1H-pyrrole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl) dicyclohexylamine salt
709031-41-4

4,5-duhydro-1H-pyrrole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl) dicyclohexylamine salt

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water
2: ammonium hydroxide / Inert atmosphere
View Scheme
C15H20N4O6*C12H23N

C15H20N4O6*C12H23N

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
With ammonium hydroxide Inert atmosphere;
lithium (2S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylate

lithium (2S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylate

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: ethyl acetate / 0.25 h / 8 °C / Inert atmosphere
1.2: 2 h / 8 - 12 °C / Inert atmosphere
2.1: ammonium hydroxide / 0.5 h / 0 - 20 °C
View Scheme
C13H17N3O3

C13H17N3O3

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
With ammonium hydroxide at 0 - 20℃; for 0.5h;1.75 g
(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one
108963-96-8

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: lithium triethylborohydride / tetrahydrofuran / 5 - 10 °C
1.2: 3 h / 120 °C
2.1: lithium hydroxide monohydrate / methanol; water / -5 - 30 °C
3.1: 4-methyl-morpholine; methanesulfonyl chloride; ammonia / -15 - -8 °C
View Scheme
Multi-step reaction with 3 steps
1.1: lithium triethylborohydride / toluene; tetrahydrofuran / 3 h / -70 - -60 °C / Inert atmosphere
1.2: 3.33 h / -60 - 20 °C
2.1: water; lithium hydroxide / methanol / 2 h / 0 - 20 °C
3.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 3 h / -20 - 0 °C
3.2: 0 - 20 °C
View Scheme
L-Pyroglutamic acid
98-79-3

L-Pyroglutamic acid

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / -5 - 30 °C
2.1: triethylamine / toluene / -5 - 0 °C
2.2: -5 - 30 °C
3.1: lithium triethylborohydride / tetrahydrofuran / 5 - 10 °C
3.2: 3 h / 120 °C
4.1: lithium hydroxide monohydrate / methanol; water / -5 - 30 °C
5.1: 4-methyl-morpholine; methanesulfonyl chloride; ammonia / -15 - -8 °C
View Scheme
Multi-step reaction with 5 steps
1.1: thionyl chloride / 5 h / -5 - 0 °C / Large scale
2.1: dmap / toluene / 3 h / 25 °C / Large scale
3.1: lithium triethylborohydride / toluene; tetrahydrofuran / 0.5 h / -45 °C / Large scale
3.2: 3 h / 25 °C / Large scale
4.1: lithium hydroxide monohydrate / water; ethanol / 2 h / 25 °C / Large scale
5.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -25 - -20 °C / Large scale
5.2: 3 h / 0 - 20 °C / Large scale
View Scheme
methyl (S)-pyroglutamate
4931-66-2

methyl (S)-pyroglutamate

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine / toluene / -5 - 0 °C
1.2: -5 - 30 °C
2.1: lithium triethylborohydride / tetrahydrofuran / 5 - 10 °C
2.2: 3 h / 120 °C
3.1: lithium hydroxide monohydrate / methanol; water / -5 - 30 °C
4.1: 4-methyl-morpholine; methanesulfonyl chloride; ammonia / -15 - -8 °C
View Scheme
(S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate
83548-46-3

(S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium hydroxide monohydrate / methanol; water / -5 - 30 °C
2: 4-methyl-morpholine; methanesulfonyl chloride; ammonia / -15 - -8 °C
View Scheme
Multi-step reaction with 2 steps
1.1: water; lithium hydroxide / methanol / 2 h / 0 - 20 °C
2.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 3 h / -20 - 0 °C
2.2: 0 - 20 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

tetramethylammonium trifluoromethanesulphonate
25628-09-5

tetramethylammonium trifluoromethanesulphonate

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
361440-67-7

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
With n-butyllithium; C40H54NiP2 In tetrahydrofuran; hexane at 0 - 20℃; for 16h; Reagent/catalyst; Solvent; Inert atmosphere;93%
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

diiodomethane
75-11-6

diiodomethane

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
361440-67-7

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Stage #1: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester; diiodomethane With diethylzinc In water; ethyl acetate; toluene at -10 - 0℃; for 105h; Inert atmosphere;
Stage #2: With trifluoroacetic acid In water; ethyl acetate; toluene at -10 - 16℃; for 1.66667h; Reagent/catalyst; Inert atmosphere;
70%
Stage #1: diiodomethane With copper(I) bromide; zinc In tert-butyl methyl ether at 20℃; for 0.5h; Simmons-Smith Cyclopropanation; Inert atmosphere;
Stage #2: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester In tert-butyl methyl ether at 20℃; for 4.5h; Simmons-Smith Cyclopropanation; Inert atmosphere;
68%
Stage #1: diiodomethane With diethylzinc In 1,2-dimethoxyethane; dichloromethane; toluene at -30 - -25℃; for 0.75h; Simmons-Smith Reaction;
Stage #2: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester In 1,2-dimethoxyethane; dichloromethane; toluene at 22 - 24℃;
Stage #3: With sodium hydrogencarbonate In 1,2-dimethoxyethane; dichloromethane; water; toluene at 15℃; for 1h;
55%
With diethylzinc In 1,2-dimethoxyethane; dichloromethane at -30 - 20℃; Simmons-Smith Cyclopropanation; stereoselective reaction;45%
Stage #1: diiodomethane With diethylzinc In 1,2-dimethoxyethane; dichloromethane; toluene at -30 - -20℃; for 0.75h; Large scale;
Stage #2: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester In 1,2-dimethoxyethane; dichloromethane; toluene at -25 - 24℃; Large scale;
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

[1S-(<α, 3<β, 5<α)-3-aminocarbonyl]-2-azabicyclo [3.1.0] hexane-2-carboxylic acid 1,1-dimethylethyl ester

[1S-(<α, 3<β, 5<α)-3-aminocarbonyl]-2-azabicyclo [3.1.0] hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Stage #1: diiodomethane With diethylzinc In 1,2-dimethoxyethane; dichloromethane; toluene at -30 - 25℃; for 0.75h; Simmons-Smith Reaction;
Stage #2: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester In 1,2-dimethoxyethane; dichloromethane; toluene at 22 - 24℃;
55%
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(13)C(2)H2I2
1217038-24-8

(13)C(2)H2I2

(1S,3S,5S)-tert-butyl 3-carbamoyl-6-[13CD2]-2-azabicyclo[3.1.0]hexane-2-carboxylate
1572922-54-3

(1S,3S,5S)-tert-butyl 3-carbamoyl-6-[13CD2]-2-azabicyclo[3.1.0]hexane-2-carboxylate

Conditions
ConditionsYield
Stage #1: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester With diethylzinc In dichloromethane; toluene at 0℃; for 0.5h; Inert atmosphere;
Stage #2: (13)C(2)H2I2 In dichloromethane; toluene at 0 - 20℃; for 17h; Simmons-Smith Cyclopropanation; Inert atmosphere;
40%
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

<14C>methylene iodide
58401-84-6

<14C>methylene iodide

(1S,3S,5S)-tert-butyl 3-carbamoyl-6-[14C]-2-azabicyclo[3.1.0]hexane-2-carboxylate

(1S,3S,5S)-tert-butyl 3-carbamoyl-6-[14C]-2-azabicyclo[3.1.0]hexane-2-carboxylate

Conditions
ConditionsYield
With water; diethylzinc In dichloromethane; toluene; pentane at -10 - 20℃; for 21h; Simmons-Smith Cyclopropanation; Inert atmosphere;10.2%
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

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 4 steps
1.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
2.1: isopropyl alcohol / 60 °C
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
4.2: 18 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: diethylzinc / dichloromethane; toluene; 1,2-dimethoxyethane / 0.75 h / -30 - -20 °C / Large scale
1.2: -25 - 24 °C / Large scale
2.1: hydrogenchloride / water; tetrahydrofuran; ethyl acetate / 18 h / 20 °C
3.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice
3.2: 20 °C
4.1: pyridine; trifluoroacetic anhydride / 0.5 h / Cooling with ice
4.2: 7.55 h / Cooling
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(R)-N-Boc-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile
1564266-92-7

(R)-N-Boc-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
2.1: isopropyl alcohol / 60 °C
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
4.2: 18 h / 20 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

saxagliptin

saxagliptin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
2.1: isopropyl alcohol / 60 °C
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
4.2: 18 h / 20 °C
5.1: hydrogenchloride / isopropyl alcohol; water / 1.5 h / 65 °C
View Scheme
Multi-step reaction with 6 steps
1.1: diethylzinc / dichloromethane; toluene; 1,2-dimethoxyethane / 0.75 h / -30 - -20 °C / Large scale
1.2: -25 - 24 °C / Large scale
2.1: hydrogenchloride / water; tetrahydrofuran; ethyl acetate / 18 h / 20 °C
3.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice
3.2: 20 °C
4.1: pyridine; trifluoroacetic anhydride / 0.5 h / Cooling with ice
4.2: 7.55 h / Cooling
5.1: dichloromethane / methanol / 20 °C / Inert atmosphere
6.1: water; dichloromethane
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(R)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile

(R)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
2.1: isopropyl alcohol / 60 °C
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
4.2: 18 h / 20 °C
5.1: hydrogenchloride / isopropyl alcohol; water / 1.5 h / 65 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
2: isopropyl alcohol / 60 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

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
Multi-step reaction with 3 steps
1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
2: isopropyl alcohol / 60 °C
3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
View Scheme
Multi-step reaction with 3 steps
1.1: diethylzinc / dichloromethane; toluene; 1,2-dimethoxyethane / 0.75 h / -30 - -20 °C / Large scale
1.2: -25 - 24 °C / Large scale
2.1: hydrogenchloride / water; tetrahydrofuran; ethyl acetate / 18 h / 20 °C
3.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice
3.2: 20 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(R)-N-Boc-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinamide
1528611-63-3

(R)-N-Boc-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
2: isopropyl alcohol / 60 °C
3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

tert-butyl((S)-2-((1S,3S,5S)-3-(6-[13CD2])-cyano-2-azabicyclo[3.1.0]hexan-2-yl)-1-(3,5-dihydroxyadamantan-1-yl)-2-oxoethyl)carbamate
1572922-58-7

tert-butyl((S)-2-((1S,3S,5S)-3-(6-[13CD2])-cyano-2-azabicyclo[3.1.0]hexan-2-yl)-1-(3,5-dihydroxyadamantan-1-yl)-2-oxoethyl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: diethylzinc / dichloromethane; toluene / 0.5 h / 0 °C / Inert atmosphere
1.2: 17 h / 0 - 20 °C / Inert atmosphere
2.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
3.1: hydrogenchloride / 1,4-dioxane / 1.2 h / 47 °C / Inert atmosphere
4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

C17(13)CH23(2)H2N3O3*ClH
1572922-53-2

C17(13)CH23(2)H2N3O3*ClH

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: diethylzinc / dichloromethane; toluene / 0.5 h / 0 °C / Inert atmosphere
1.2: 17 h / 0 - 20 °C / Inert atmosphere
2.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
3.1: hydrogenchloride / 1,4-dioxane / 1.2 h / 47 °C / Inert atmosphere
4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide
5.1: hydrogenchloride / water; isopropyl alcohol
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

C22(14)CH33N3O4

C22(14)CH33N3O4

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: diethylzinc; water / dichloromethane; pentane; toluene / 21 h / -10 - 20 °C / Inert atmosphere
2: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
3: hydrogenchloride / 1,4-dioxane / 1.2 h / 47 °C / Inert atmosphere
4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(1S,3S,5S)-tert-butyl 3-cyano-6-[14C]-2-azabicyclo[3.1.0]hexane-2-carboxylate

(1S,3S,5S)-tert-butyl 3-cyano-6-[14C]-2-azabicyclo[3.1.0]hexane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethylzinc; water / dichloromethane; pentane; toluene / 21 h / -10 - 20 °C / Inert atmosphere
2: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(1S,3S,5S)-6-[14C]-2-azabicyclo[3.1.0]hexane-3-carbonitrile hydrochloride

(1S,3S,5S)-6-[14C]-2-azabicyclo[3.1.0]hexane-3-carbonitrile hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diethylzinc; water / dichloromethane; pentane; toluene / 21 h / -10 - 20 °C / Inert atmosphere
2: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
3: hydrogenchloride / 1,4-dioxane / 1.2 h / 47 °C / Inert atmosphere
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

6-[14C]-saxagliptin

6-[14C]-saxagliptin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: diethylzinc; water / dichloromethane; pentane; toluene / 21 h / -10 - 20 °C / Inert atmosphere
2.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
3.1: hydrogenchloride / 1,4-dioxane / 1.2 h / 47 °C / Inert atmosphere
4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide
5.1: hydrogenchloride / water; isopropyl alcohol
5.2: 10 - 20 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(1S,3S,5S)-tert-butyl 3-cyano-6-[13CD2]-2-azabicyclo[3.1.0]hexane-2-carboxylate
1572922-55-4

(1S,3S,5S)-tert-butyl 3-cyano-6-[13CD2]-2-azabicyclo[3.1.0]hexane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: diethylzinc / dichloromethane; toluene / 0.5 h / 0 °C / Inert atmosphere
1.2: 17 h / 0 - 20 °C / Inert atmosphere
2.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(1S,3S,5S)-6-[13CD2]-2-azabicyclo[3.1.0]hexane-3-carbonitrile hydrochloride
1572922-56-5

(1S,3S,5S)-6-[13CD2]-2-azabicyclo[3.1.0]hexane-3-carbonitrile hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: diethylzinc / dichloromethane; toluene / 0.5 h / 0 °C / Inert atmosphere
1.2: 17 h / 0 - 20 °C / Inert atmosphere
2.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
3.1: hydrogenchloride / 1,4-dioxane / 1.2 h / 47 °C / Inert atmosphere
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