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

Base Information

• Chemical Name: (1S,3S)-(-)-methyl 2,9-dibenzyl-3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate
• CAS No.: 119184-22-4
• Molecular Formula: C₃₁H₃₂N₂O₄
• Molecular Weight: 496.606
• Mol file: 119184-22-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (1S,3S)-(-)-methyl 2,9-dibenzyl-3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate 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: 78.0%

(+)-cis-methyl 2,9-dibenzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate (142230-29-3) → 2,9-Dibenzyl-1-(2-methoxycarbonyl-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester (119184-21-3,119184-22-4,142230-29-3,142230-30-6)

Guidance literature:

With methanol; sodium hydride; In toluene; for 1.3h; Heating;

Reference yield:

(S)-3-(1-Benzyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester (129708-73-2) → (1S,3S)-(-)-methyl 2,9-dibenzyl-3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate (119184-22-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / sodium borohydride / methanol / 1 h / 25 °C

2: 67 percent / benzene; dioxane / 24 h / Heating

3: 34 g / chlorotrimethylsilane / 25 °C

With sodium tetrahydroborate; chloro-trimethyl-silane; In 1,4-dioxane; methanol; benzene;

DOI:10.1021/ja00169a033

Reference yield:

(S)-(-)-N,N'-dibenzyltryptophan methyl ester (119184-20-2) → (1S,3S)-(-)-methyl 2,9-dibenzyl-3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate (119184-22-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / benzene; dioxane / 24 h / Heating

2: 34 g / chlorotrimethylsilane / 25 °C

With chloro-trimethyl-silane; In 1,4-dioxane; benzene;

DOI:10.1021/ja00169a033

upstream raw materials:

diazomethane

α-ketoglutaric acid

(S)-(-)-N,N'-dibenzyltryptophan methyl ester

methanol

Downstream raw materials:

(6R,10S)-(-)-methyl 5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-8-carboxylate

C₃₀H₂₈N₂O₃

(6R,10R)-(-)-methyl 5-benzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-8-carboxylate

(6R,10R)-(-)-5-benzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole