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

Base Information

• Chemical Name: (6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole
• CAS No.: 302356-98-5
• Molecular Formula: C₂₂H₂₂N₂O
• Molecular Weight: 330.429

Synonyms:(6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

Chemical Property of (6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

Chemical Property:

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Technology Process of (6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

There total 18 articles about (6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole 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: 91.0%

(6S,10S)-(-)-methyl-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-8-carboxylate (2738-25-2,123806-88-2,123806-89-3) → (6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (302356-98-5)

Guidance literature:

With hydrogenchloride; acetic acid; for 5h; Heating;

Reference yield: 80.0%

(1R,3S)-2-Benzyl-1-(2-methoxycarbonyl-ethyl)-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester (142292-54-4) → (6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (302356-98-5)

Guidance literature:

(1R,3S)-2-Benzyl-1-(2-methoxycarbonyl-ethyl)-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester; With sodium hydride; In methanol; toluene; at 110 ℃; for 3h;

With hydrogenchloride; In acetic acid; for 8h; Heating;

DOI:10.1016/S0040-4039(00)01061-3

Reference yield:

D-(+)-Na-methyl-Nb-benzyltryptophan methyl ester (120053-66-9) → (6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (302356-98-5)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene / 10 h / Heating

2: NaH / toluene; methanol / 12 h / Heating

3: H₂O / acidic conditions

With sodium hydride; In methanol; water; toluene;

upstream raw materials:

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

(1R,3S)-2-Benzyl-1-(2-methoxycarbonyl-ethyl)-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

methyl N-benzyl-L-tryptophanate

N_b-benzylidene-L-tryptophan methyl ester

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