(1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole

Base Information

• Chemical Name: (1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole
• CAS No.: 111596-26-0
• Molecular Formula: C₂₃H₂₃N₃O₂
• Molecular Weight: 373.455

Synonyms:(1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole

Chemical Property of (1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole

Chemical Property:

Purity/Quality:

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Technology Process of (1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole

There total 5 articles about (1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 44.0%

benzyl bromide (100-39-0) + (1RS,3S)-3-(Cyanomethyl)-1-<(methoxycarbonyl)methyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole (117565-72-7,117565-73-8) → (1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole (111596-26-0) + (1R,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole (111596-27-1)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; for 96h; Yields of byproduct given; Heating;

DOI:10.1039/a606081a

Reference yield:

(3S)-3-amino-4-(1H-indol-3-yl)butanenitrile (66087-99-8) → (1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole (111596-26-0)

Guidance literature:

Multi-step reaction with 3 steps

1: CHCl₃ / 100 h / Heating

2: TFA / 0.5 h / 0 °C

3: 44 percent / NaHCO₃ / CH₂Cl₂ / 96 h / Heating

With sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; chloroform;

DOI:10.1039/a606081a

Reference yield:

(Z)-3-[(S)-2-Cyano-1-(1H-indol-3-ylmethyl)-ethylamino]-acrylic acid methyl ester → (1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole (111596-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / 0.5 h / 0 °C

2: 44 percent / NaHCO₃ / CH₂Cl₂ / 96 h / Heating

With sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane;

DOI:10.1039/a606081a

upstream raw materials:

benzyl bromide

(1RS,3S)-3-(Cyanomethyl)-1-<(methoxycarbonyl)methyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole

(3S)-3-amino-4-(1H-indol-3-yl)butanenitrile

propynoic acid methyl ester

Downstream raw materials:

(1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole

(6S,10S,8E)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooctindole-9-carbaldehyde

C₂₃H₂₄N₂O

(6S,10S,8E)-12-Benzyl-9-cyano-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooct[b]indole

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