(1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-9-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>-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole
• CAS No.: 111619-15-9
• Molecular Formula: C₂₄H₂₅N₃O₂
• Molecular Weight: 387.481

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

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

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Useful:

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

There total 8 articles about (1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-9-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: 92.0%

(1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole (111596-26-0) + methyl iodide (74-88-4) → (1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole (111619-15-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; 1.) 0 deg C, 1 h, 2.) r.t., 30 min;

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>-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole (111619-15-9)

Guidance literature:

Multi-step reaction with 4 steps

1: CHCl₃ / 100 h / Heating

2: TFA / 0.5 h / 0 °C

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

4: 92 percent / NaH / dimethylformamide / 1.) 0 deg C, 1 h, 2.) r.t., 30 min

With sodium hydride; sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1039/a606081a

Reference yield:

(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>-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole (111619-15-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 44 percent / NaHCO₃ / CH₂Cl₂ / 96 h / Heating

2: 92 percent / NaH / dimethylformamide / 1.) 0 deg C, 1 h, 2.) r.t., 30 min

With sodium hydride; sodium hydrogencarbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/a606081a

upstream raw materials:

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

methyl iodide

benzyl bromide

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

Downstream raw materials:

C₂₃H₂₁N₃O

C₂₃H₂₁N₃O

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

C₂₃H₂₄N₂O

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