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239463-85-5

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CAS No.: 239463-85-5
Name: 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate
Article Data: 8
Molecular Structure:
Molecular Structure of 239463-85-5 (5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate)
Formula: C22H25N3O2.C4H6O6
Molecular Weight: 513.547
Synonyms: 3-{5[(2R)-2-aminoprppyl]-7-cyano-2,3-dihydro-1H-indol-1-yl}propyl benzoate monotartaric acid salt; (R)-5-(2-aminopropyl)-1-(3-benzoyloxypropyl) Indoline-7-Carbonitrile Tartaric acid; 5-[(2R)-2-AMINOPROPYL]-1-[3-(BENZOYLOXY)PROPYL]-2,3-DIHYDRO-1H-INDOLE-7-CARBONITRILE (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE; (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate; 3-(5-((R)-2-aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate L-tartrate; 1-(3-benzoyloxypropyl)-7-cyano-5-(2-aminopropyl)-2,3-dihydroindole; 查看更多英文别名 收起
EINECS: 688-292-1
PSA: 194.41000
LogP: 1.70028
Related products
Synthetic route
87-69-4

L-Tartaric acid

C38H39N3O4

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%
87-69-4

L-Tartaric acid

C42H41N3O4

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%
87-69-4

L-Tartaric acid

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

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%
87-69-4

L-Tartaric acid

1338365-54-0

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

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
350797-56-7

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

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
350797-53-4

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

A

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

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
350797-54-5

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

A

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

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
350797-55-6

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

A

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

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
350797-56-7

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

A

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

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
87-69-4

L-Tartaric acid

1338365-54-0

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

A

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

Conditions
ConditionsYield
In water; acetone at 25 - 65℃; Resolution of racemate;A n/a
B n/a
...Expand
Raw Materials
350797-56-7
87-69-4
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