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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

5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate

Cas:239463-85-5

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

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Jinan Finer Chemical Co., Ltd

Product Description Product website: http://www.finerchem.com Product Name 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indo

Hangzhou Think Chemical Co. Ltd

5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate CAS No.:239463-85-5 Name: 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile

Hangzhou Dingyan Chem Co., Ltd

Items Standard Result Appearance Off-white to light yellow-green powder Light yellow-green powder Solubility

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

Shanghai Seasonsgreen Chemical Co.,Ltd

Shanghai Seasonsgreen Chemical is a high-tech research and development, production, sale and custom synthesis set in one high-tech chemical products enterprises. Our sales and marketing division is located in Shanghai, serving international pharmaceu

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

Henan Tianfu Chemical Co., Ltd.

Our company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.O

Hebei Nengqian Chemical Import and Export Co., LTD

Our Advantage Rich Experience Our products are sold all over Europe,North&South America, Sino-East, Asia and pacific area as well as Africa,we establish long term. Quality service Company cooperates with research institutes. We strictly con

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 239463-85-5 with best quality

Cas:239463-85-5

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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LIDE PHARMACEUTICALS LIMITED

Advantage : LIDE PHARMACEUTICALS LTD. is a mid-small manufacturing-type enterprise, engaged in pharmaceutical intermediates of R&D, custom-made and production, and also involving trading chemicals for export. We have established the R&amp

Hangzhou Sartort Biopharma Co., Ltd

Appearance:Almost white powder or yellow powder Storage:R.T Package:25kg/Barrel Application:Silodosin Intermediate Transportation:Express/Sea/Air Port:Any port in China

Silodosin Intermediate cas 239463-85-5

Cas:239463-85-5

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

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 service is

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 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indo

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

Hangzhou Fonlynn Health Technology Co., Ltd.

Packing: According to customer requirements Delivery time: In stock or depands Port of shipment: Ningbo/Shanghai/Qingdao OEM/ODM:Welcome Sample:We can offer our existing samples at once Appearance:light yellow green powder/ Refer to COA Storage

Baoji Guokang Healthchem co.,ltd

Our company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At prese

5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate

Cas:239463-85-5

Min.Order:1 Kilogram

FOB Price: $85.0 / 97.0

Type:Trading Company

inquiry

Qingdao Beluga Import and Export Co., LTD

Beluga chemical professional supply 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate CAS 239463-85-5 Why choose Beluga chemical 1. Beluga Chemical has a professional RESEARCH a

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

Hebei Quanhe Biotechnology Co. LTD

1. Timely and efficient service to ensure communication with customers 2. Produce products of different specifications and sizes according to your requirements. 3. Quality procedures and standards recognized by SGS. Advanced plant equipment ensures s

5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate

Cas:239463-85-5

Min.Order:1 Kilogram

FOB Price: $40.0 / 50.0

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

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

Triumph International Development Limilted

Triumph has the complete production of G- KG - MT service chain,we can make the new technology into productivity quickly in the research and development of new products. Main Service 1.Own made fine chemical products 2.Out sourcing and qua

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 have s

Win-Win chemical Co.Ltd

Stock products, own laboratory Package:Grams, Kilograms Application:For R&D Transportation:According to customer request Port:Shanghai

5-(2R,3R)-2,3-dihydroxybutanedioate cas no.239463-85-5 0.98

Cas:239463-85-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Taizhou Crene Biotechnology co.ltd

Our company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-

Silodoxin intermediates 239463-85-5

Cas:239463-85-5

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Afine Chemicals Limited

Company Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments

SHANGHAI T&W PHARMACEUTICAL CO., LTD.

A substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc

Hangzhou J&H Chemical Co., Ltd.

J&H CHEM 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. J&H CHEM has some Manufacturing base in Jia

Kono Chem Co.,Ltd

Product Name: 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate Synonyms: 5-[(2R…Appearance:Solid powder Storage:Sealed,light and oxygen resistant Package:aluminum foil bag,carton

Synthetic route

L-Tartaric acid
87-69-4

L-Tartaric acid

C38H39N3O4

C38H39N3O4

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Stage #1: C38H39N3O4 With palladium on activated charcoal; hydrogen
Stage #2: L-Tartaric acid Inert atmosphere;
33.3%
L-Tartaric acid
87-69-4

L-Tartaric acid

C42H41N3O4

C42H41N3O4

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Stage #1: C42H41N3O4 With palladium on activated charcoal; hydrogen
Stage #2: L-Tartaric acid Inert atmosphere;
30.9%
L-Tartaric acid
87-69-4

L-Tartaric acid

3-(5-(2-((tert-butoxycarbonyl)amino)propyl)-7-cyanoindolin-1-yl)propylbenzoate

3-(5-(2-((tert-butoxycarbonyl)amino)propyl)-7-cyanoindolin-1-yl)propylbenzoate

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Stage #1: 3-(5-(2-((tert-butoxycarbonyl)amino)propyl)-7-cyanoindolin-1-yl)propylbenzoate With hydrogenchloride In chloroform; water at 25 - 30℃; for 5h;
Stage #2: L-Tartaric acid In water; acetone at 20 - 25℃; for 12h;
23.5%
L-Tartaric acid
87-69-4

L-Tartaric acid

5-(2-aminopropyl)-1-[3-(benzoyloxy)propyl]-2,3-dihydro-7-cyano-1H-indole
1338365-54-0

5-(2-aminopropyl)-1-[3-(benzoyloxy)propyl]-2,3-dihydro-7-cyano-1H-indole

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
In tetrahydrofuran; water at 20 - 65℃; Product distribution / selectivity;
In water; acetone at 20℃; for 49h;2.05 g
1-(3-benzoyloxypropyl)-7-cyano-5-(2-nitropropyl)-2,3-dihydroindole
350797-56-7

1-(3-benzoyloxypropyl)-7-cyano-5-(2-nitropropyl)-2,3-dihydroindole

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride; zinc / water; methanol / 20 h / 60 - 65 °C
2: water; tetrahydrofuran / 20 - 65 °C
View Scheme
Multi-step reaction with 2 steps
1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
2: water; acetone / 49 h / 20 °C
View Scheme
1-(3-benzoyloxypropyl)-5-(2-nitro-1-propenyl)-2,3-dihydroindole
350797-53-4

1-(3-benzoyloxypropyl)-5-(2-nitro-1-propenyl)-2,3-dihydroindole

A

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

B

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium tetrahydroborate; potassium hydroxide / tetrahydrofuran; water / -10 - 20 °C
2.1: trichlorophosphate / 0 - 50 °C
2.2: Cooling with ice
3.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C
3.2: 2 h / 80 °C
4.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave
5.1: acetone; water / 25 - 65 °C / Resolution of racemate
View Scheme
1-(3-benzoyloxypropyl)-5-(2-nitropropyl)-2,3-dihydroindole
350797-54-5

1-(3-benzoyloxypropyl)-5-(2-nitropropyl)-2,3-dihydroindole

A

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

B

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: trichlorophosphate / 0 - 50 °C
1.2: Cooling with ice
2.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C
2.2: 2 h / 80 °C
3.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave
4.1: acetone; water / 25 - 65 °C / Resolution of racemate
View Scheme
1-(3-benzoyloxypropyl)-7-formyl-5-(2-nitropropyl)-2,3-dihydroindole
350797-55-6

1-(3-benzoyloxypropyl)-7-formyl-5-(2-nitropropyl)-2,3-dihydroindole

A

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

B

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C
1.2: 2 h / 80 °C
2.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave
3.1: acetone; water / 25 - 65 °C / Resolution of racemate
View Scheme
1-(3-benzoyloxypropyl)-7-cyano-5-(2-nitropropyl)-2,3-dihydroindole
350797-56-7

1-(3-benzoyloxypropyl)-7-cyano-5-(2-nitropropyl)-2,3-dihydroindole

A

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

B

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave
2: acetone; water / 25 - 65 °C / Resolution of racemate
View Scheme
L-Tartaric acid
87-69-4

L-Tartaric acid

5-(2-aminopropyl)-1-[3-(benzoyloxy)propyl]-2,3-dihydro-7-cyano-1H-indole
1338365-54-0

5-(2-aminopropyl)-1-[3-(benzoyloxy)propyl]-2,3-dihydro-7-cyano-1H-indole

A

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

B

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

Conditions
ConditionsYield
In water; acetone at 25 - 65℃; Resolution of racemate;A n/a
B n/a
benzoic acid
65-85-0

benzoic acid

A

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

B

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: triethylamine / N,N-dimethyl-formamide / 20 °C
1.2: 3 h / 100 °C
2.1: trichlorophosphate / 2 h / 20 °C
2.2: Cooling with ice
3.1: ammonium acetate / 20 - 100 °C
4.1: sodium tetrahydroborate; potassium hydroxide / tetrahydrofuran; water / -10 - 20 °C
5.1: trichlorophosphate / 0 - 50 °C
5.2: Cooling with ice
6.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C
6.2: 2 h / 80 °C
7.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave
8.1: acetone; water / 25 - 65 °C / Resolution of racemate
View Scheme
1-indoline
496-15-1

1-indoline

A

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

B

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: triethylamine / N,N-dimethyl-formamide / 20 °C
1.2: 3 h / 100 °C
2.1: trichlorophosphate / 2 h / 20 °C
2.2: Cooling with ice
3.1: ammonium acetate / 20 - 100 °C
4.1: sodium tetrahydroborate; potassium hydroxide / tetrahydrofuran; water / -10 - 20 °C
5.1: trichlorophosphate / 0 - 50 °C
5.2: Cooling with ice
6.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C
6.2: 2 h / 80 °C
7.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave
8.1: acetone; water / 25 - 65 °C / Resolution of racemate
View Scheme
1-(3-benzoyloxypropyl)-2,3-dihydroindole hydrochloride
350797-51-2

1-(3-benzoyloxypropyl)-2,3-dihydroindole hydrochloride

A

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

B

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: trichlorophosphate / 2 h / 20 °C
1.2: Cooling with ice
2.1: ammonium acetate / 20 - 100 °C
3.1: sodium tetrahydroborate; potassium hydroxide / tetrahydrofuran; water / -10 - 20 °C
4.1: trichlorophosphate / 0 - 50 °C
4.2: Cooling with ice
5.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C
5.2: 2 h / 80 °C
6.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave
7.1: acetone; water / 25 - 65 °C / Resolution of racemate
View Scheme
1-(3-benzoyloxypropyl)-5-formyl-2,3-dihydroindole
350797-52-3

1-(3-benzoyloxypropyl)-5-formyl-2,3-dihydroindole

A

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

B

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

5-[(2S)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile L-(+)-tartrate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: ammonium acetate / 20 - 100 °C
2.1: sodium tetrahydroborate; potassium hydroxide / tetrahydrofuran; water / -10 - 20 °C
3.1: trichlorophosphate / 0 - 50 °C
3.2: Cooling with ice
4.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C
4.2: 2 h / 80 °C
5.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave
6.1: acetone; water / 25 - 65 °C / Resolution of racemate
View Scheme
C22H25N3O5

C22H25N3O5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
2: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
3: water; acetone / 49 h / 20 °C
View Scheme
3-(indolin-1-yl)propan-1-ol

3-(indolin-1-yl)propan-1-ol

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: triethylamine / dichloromethane / 8 h / 0 - 25 °C / Inert atmosphere
2.1: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 0 °C / Inert atmosphere
2.2: 2 h / 0 - 80 °C / Inert atmosphere
3.1: ammonium acetate; acetic acid / 4 h / 80 °C
4.1: sodium tetrahydroborate / dichloromethane; methanol / 1 h / 0 - 25 °C
5.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere
5.2: 2 h / 0 - 80 °C / Inert atmosphere
6.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C
7.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
8.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
9.1: water; acetone / 49 h / 20 °C
View Scheme
3-(indolin-1-yl)propyl benzoate

3-(indolin-1-yl)propyl benzoate

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 0 °C / Inert atmosphere
1.2: 2 h / 0 - 80 °C / Inert atmosphere
2.1: ammonium acetate; acetic acid / 4 h / 80 °C
3.1: sodium tetrahydroborate / dichloromethane; methanol / 1 h / 0 - 25 °C
4.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere
4.2: 2 h / 0 - 80 °C / Inert atmosphere
5.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C
6.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
7.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
8.1: water; acetone / 49 h / 20 °C
View Scheme
1-(3-benzoyloxypropyl)-5-formyl-2,3-dihydroindole
350797-52-3

1-(3-benzoyloxypropyl)-5-formyl-2,3-dihydroindole

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: ammonium acetate; acetic acid / 4 h / 80 °C
2.1: sodium tetrahydroborate / dichloromethane; methanol / 1 h / 0 - 25 °C
3.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere
3.2: 2 h / 0 - 80 °C / Inert atmosphere
4.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C
5.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
6.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
7.1: water; acetone / 49 h / 20 °C
View Scheme
1-(3-benzoyloxypropyl)-5-(2-nitro-1-propenyl)-2,3-dihydroindole
350797-53-4

1-(3-benzoyloxypropyl)-5-(2-nitro-1-propenyl)-2,3-dihydroindole

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium tetrahydroborate / dichloromethane; methanol / 1 h / 0 - 25 °C
2.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere
2.2: 2 h / 0 - 80 °C / Inert atmosphere
3.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C
4.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
5.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
6.1: water; acetone / 49 h / 20 °C
View Scheme
1-indoline
496-15-1

1-indoline

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: potassium carbonate / acetonitrile / 12 h / 90 °C
2.1: triethylamine / dichloromethane / 8 h / 0 - 25 °C / Inert atmosphere
3.1: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 0 °C / Inert atmosphere
3.2: 2 h / 0 - 80 °C / Inert atmosphere
4.1: ammonium acetate; acetic acid / 4 h / 80 °C
5.1: sodium tetrahydroborate / dichloromethane; methanol / 1 h / 0 - 25 °C
6.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere
6.2: 2 h / 0 - 80 °C / Inert atmosphere
7.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C
8.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
9.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
10.1: water; acetone / 49 h / 20 °C
View Scheme
1-(3-benzoyloxypropyl)-5-(2-nitropropyl)-2,3-dihydroindole
350797-54-5

1-(3-benzoyloxypropyl)-5-(2-nitropropyl)-2,3-dihydroindole

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere
1.2: 2 h / 0 - 80 °C / Inert atmosphere
2.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C
3.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
4.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
5.1: water; acetone / 49 h / 20 °C
View Scheme
1-(3-benzoyloxypropyl)-7-formyl-5-(2-nitropropyl)-2,3-dihydroindole
350797-55-6

1-(3-benzoyloxypropyl)-7-formyl-5-(2-nitropropyl)-2,3-dihydroindole

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C
2: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
3: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
4: water; acetone / 49 h / 20 °C
View Scheme
C24H28N2O4

C24H28N2O4

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 1 h / 50 °C / Inert atmosphere
1.2: 3.5 h / 50 °C
2.1: hydrogenchloride / water / 12 h / Inert atmosphere; Reflux
3.1: water; methanol / 0.5 h / Inert atmosphere; Reflux
View Scheme
C24H27N3O3

C24H27N3O3

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 12 h / Inert atmosphere; Reflux
2: water; methanol / 0.5 h / Inert atmosphere; Reflux
View Scheme
5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile
239463-72-0

5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile

L-Tartaric acid
87-69-4

L-Tartaric acid

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
In methanol; water for 0.5h; Inert atmosphere; Reflux;
C24H28N2O5

C24H28N2O5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: trifluoroacetic acid; triethylsilane / toluene / 18 h / 45 °C / Inert atmosphere
2.1: trichlorophosphate / 0.5 h / Cooling with ice; Inert atmosphere
2.2: 3 h / 50 °C
3.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 1 h / 50 °C / Inert atmosphere
3.2: 3.5 h / 50 °C
4.1: hydrogenchloride / water / 10 h / Inert atmosphere; Reflux
5.1: water; methanol / 0.5 h / Inert atmosphere; Reflux
View Scheme
C24H30N2O4

C24H30N2O4

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: trichlorophosphate / 0.5 h / Cooling with ice; Inert atmosphere
1.2: 3 h / 50 °C
2.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 1 h / 50 °C / Inert atmosphere
2.2: 3.5 h / 50 °C
3.1: hydrogenchloride / water / 10 h / Inert atmosphere; Reflux
4.1: water; methanol / 0.5 h / Inert atmosphere; Reflux
View Scheme
C25H30N2O5

C25H30N2O5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 1 h / 50 °C / Inert atmosphere
1.2: 3.5 h / 50 °C
2.1: hydrogenchloride / water / 10 h / Inert atmosphere; Reflux
3.1: water; methanol / 0.5 h / Inert atmosphere; Reflux
View Scheme
C25H29N3O4

C25H29N3O4

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 10 h / Inert atmosphere; Reflux
2: water; methanol / 0.5 h / Inert atmosphere; Reflux
View Scheme
C26H32N2O5

C26H32N2O5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: trifluoroacetic acid; triethylsilane / toluene / 22 h / 45 °C / Inert atmosphere
2.1: trichlorophosphate / 0.5 h / Cooling with ice; Inert atmosphere
2.2: 3 h / 50 °C
3.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 1 h / 50 °C / Inert atmosphere
3.2: 3.5 h / 50 °C
4.1: hydrogenchloride / water / 12 h / Inert atmosphere; Reflux
5.1: water; methanol / 0.5 h / Inert atmosphere; Reflux
View Scheme
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

(R)-5-(2-aminopropyl)-1-(3-hydroxypropyl)indoline-7-carbonitrile
1401991-17-0

(R)-5-(2-aminopropyl)-1-(3-hydroxypropyl)indoline-7-carbonitrile

Conditions
ConditionsYield
With potassium hydroxide In methanol for 2h; Reflux;100%
With water; potassium hydroxide In methanol at 20℃;
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile
239463-72-0

5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile

Conditions
ConditionsYield
With sodium carbonate In water; ethyl acetate for 2h; Large scale;99%
With sodium hydroxide In dichloromethane; water at 10℃; pH=11;97.5%
With sodium carbonate In water pH=10;1.25 g
With potassium carbonate In water pH=10;
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene
160969-03-9

1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene

2,3-dihydro-1-[3-(benzoyloxy)propyl]-5-[(2R)-2-[[2-[(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile
885340-11-4

2,3-dihydro-1-[3-(benzoyloxy)propyl]-5-[(2R)-2-[[2-[(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile

Conditions
ConditionsYield
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In water; ethyl acetate at 20℃; for 1h;
Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With tetrabutylammomium bromide; sodium carbonate In acetonitrile at 75 - 85℃; for 30h; Reagent/catalyst; Solvent;
85%
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In water; ethyl acetate at 20℃; for 1h;
Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With sodium carbonate In isopropyl alcohol at 80℃; Product distribution / selectivity;
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In N,N-dimethyl acetamide; acetonitrile at 80℃; for 0.5h;
Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With potassium iodide at 80℃; for 10h;
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In N,N-dimethyl acetamide; acetonitrile at 80℃; for 0.5h;
Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With potassium iodide In N,N-dimethyl acetamide; acetonitrile at 80℃; for 10h;
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In water; ethyl acetate for 2h; Reflux;
Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With sodium carbonate In toluene Reflux;
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

5-[(2R)-2-(tert-butoxycarbonyl)aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-7-cyano-1H-indole

5-[(2R)-2-(tert-butoxycarbonyl)aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-7-cyano-1H-indole

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2h;84.48%
With potassium carbonate In dichloromethane; water at 15 - 25℃; for 5h;457 g
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

oxalic acid
144-62-7

oxalic acid

1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene
160969-03-9

1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene

1-(3-hydroxypropyl)-5-(2R)-2-{2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}aminopropyl-2,3-dihydro-1H-indole-7-carbonitrile oxalic acid

1-(3-hydroxypropyl)-5-(2R)-2-{2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}aminopropyl-2,3-dihydro-1H-indole-7-carbonitrile oxalic acid

Conditions
ConditionsYield
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In N,N-dimethyl acetamide; acetonitrile at 80℃; for 0.5h;
Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With potassium iodide In N,N-dimethyl acetamide; acetonitrile at 80℃; for 10h;
Stage #3: oxalic acid at 50℃; for 0.5h; Solvent;
82%
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

succinic acid
110-15-6

succinic acid

1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene
160969-03-9

1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene

1-(3-hydroxypropyl)-5-(2R)-2-{2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}aminopropyl-2,3-dihydro-1H-indole-7-carbonitrile succinic acid

1-(3-hydroxypropyl)-5-(2R)-2-{2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}aminopropyl-2,3-dihydro-1H-indole-7-carbonitrile succinic acid

Conditions
ConditionsYield
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In N,N-dimethyl acetamide; acetonitrile at 80℃; for 0.5h;
Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With potassium iodide In N,N-dimethyl acetamide; acetonitrile at 80℃; for 10h;
Stage #3: succinic acid at 50℃; for 0.5h;
81%
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene
160969-03-9

1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene

1-(3-hydroxypropyl)-5-(2R)-2-{2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}aminopropyl-2,3-dihydro-1H-indole-7-carbonitrile fumaric acid

1-(3-hydroxypropyl)-5-(2R)-2-{2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}aminopropyl-2,3-dihydro-1H-indole-7-carbonitrile fumaric acid

Conditions
ConditionsYield
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In N,N-dimethyl acetamide; acetonitrile at 80℃; for 0.5h;
Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With potassium iodide In N,N-dimethyl acetamide; acetonitrile at 80℃; for 10h;
Stage #3: (2E)-but-2-enedioic acid at 50℃; for 0.5h;
81%
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

L-Tartaric acid
87-69-4

L-Tartaric acid

1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene
160969-03-9

1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene

3-(7-cyano-5-[(2R)-2-(2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino)propyl]-2,3-dihydro-1H-indol-1-yl)propylbenzoate (2R,3R)-tartrate salt

3-(7-cyano-5-[(2R)-2-(2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino)propyl]-2,3-dihydro-1H-indol-1-yl)propylbenzoate (2R,3R)-tartrate salt

Conditions
ConditionsYield
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt; 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With sodium carbonate In acetonitrile for 24h; Reflux;
Stage #2: L-Tartaric acid In ethanol at 20℃; for 5h;
79.3%
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In acetic acid butyl ester; water at 45℃;
Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene In acetic acid butyl ester; water for 18h; Reflux;
Stage #3: L-Tartaric acid In acetic acid butyl ester at 80℃;
4.6 g
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
239463-85-5

5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt

1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene
160969-03-9

1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene

A

2,3-dihydro-1-[3-(benzoyloxy)propyl]-5-[(2R)-2-[[2-[(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile
885340-11-4

2,3-dihydro-1-[3-(benzoyloxy)propyl]-5-[(2R)-2-[[2-[(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile

B

C40H41F6N3O7

C40H41F6N3O7

Conditions
ConditionsYield
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In water; ethyl acetate at 20℃; for 2h;
Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With sodium carbonate In tert-butyl alcohol for 24h; Heating / reflux;
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