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239463-85-5

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  • 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

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

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  • High purity 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

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  • High purity 239463-85-5 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

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  • High Quality Oled CAS 239463-85-5 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

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  • lower price High quality 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

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

    Cas No: 239463-85-5

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239463-85-5 Usage

Uses

5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-Dihydroxybutanedioate is an intermediate of Silodosin (S465000) which is an α1a-adrenoceptor antagonist and used in the treatment of benign prostatic hypertophy.

Check Digit Verification of cas no

The CAS Registry Mumber 239463-85-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,3,9,4,6 and 3 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 239463-85:
(8*2)+(7*3)+(6*9)+(5*4)+(4*6)+(3*3)+(2*8)+(1*5)=165
165 % 10 = 5
So 239463-85-5 is a valid CAS Registry Number.

239463-85-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-[5-[(2R)-2-aminopropyl]-7-cyano-2,3-dihydroindol-1-yl]propyl benzoate,(2R,3R)-2,3-dihydroxybutanedioic acid

1.2 Other means of identification

Product number -
Other names 3-{5[(2R)-2-aminoprppyl]-7-cyano-2,3-dihydro-1H-indol-1-yl}propyl benzoate monotartaric acid salt

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:239463-85-5 SDS

239463-85-5Synthetic 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;

239463-85-5Relevant articles and documents

THE MANUFACTURING METHOD OF INTERMEDIATE FOR SYNTHESIS OF SILODOSIN AND THE MANUFACTURING METHOD OF SILODOSIN

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, (2020/03/31)

The present invention relates to a method for producing an intermediate for the synthesis, of a cilodosin, and a method for producing, a cilodosin using the, same, which can be used in a method for producing a cilodosin, which can increase the price competitiveness and can reduce. risk factors in the production process, facilitate mass production, and obtain a high purity of xylodosin. (by machine translation)

Method for preparing silodosin intermediate

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Paragraph 0039; 0049; 0058; 0067; 0076; 0084; 0085, (2019/01/06)

The invention discloses a method for preparing silodosin intermediate 5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indolyl-7-nitrily-L-(+)-tartrate. The method specifically comprisesthe steps of recovering waste filter liquor in a resolution reaction, subjecting the filter liquor to catalyzed racemation by a palladium catalyst so as to prepare a raw material, i.e., 5-[2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indolyl-7-nitrile, and then, at least repeating resolution once, thereby increasing the yield of the resolution product, i.e., a key intermediate of silodosin, i.e., 5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indolyl-7-nitrily-L-(+)-tartrate. The target product prepared by the method disclosed by the invention is high in yield and low in cost, preconceptions in the prior art are overcome, and thus, the method is more applicable to industrial production.

Method for preparing silodosin midbody

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, (2016/10/10)

The invention discloses a method for preparing a silodosin midbody. The silodosin midbody is the compound shown in the formula (1) and prepared with indoline derivative and R-alanine derivative which are easy to obtain as starting materials through Friedel-Crafts acylation reaction, reduction reaction, formylation reaction, oximation reaction, dehydration reaction, hydrolysis reaction and salt forming reaction. The compound is used for preparing silodosin. Silodosin is used for treating urination disorder related to benign prostatic hyperplasia. The method has the advantages that raw materials are cheap and easy to obtain, operation is easy, yield is high, production cost is reduced, and the method is suitable for large-scale industrial production.

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