(6S,10S)-(-)-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indole-8-carboxylate

Base Information

• Chemical Name: (6S,10S)-(-)-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indole-8-carboxylate
• CAS No.: 197143-14-9
• Molecular Formula: C₂₃H₂₂N₂O₃
• Molecular Weight: 374.439

Synonyms:(6S,10S)-(-)-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indole-8-carboxylate

Chemical Property of (6S,10S)-(-)-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indole-8-carboxylate

Chemical Property:

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Technology Process of (6S,10S)-(-)-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indole-8-carboxylate

There total 8 articles about (6S,10S)-(-)-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indole-8-carboxylate 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,3R)-(-)-methyl 2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate (84094-74-6) → (6S,10S)-(-)-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indole-8-carboxylate (197143-14-9)

Guidance literature:

With sodium methylate; In toluene; for 60h; Heating;

DOI:10.1016/S0040-4039(97)01603-1

Reference yield:

D-(+)-Nbbenzyltryptophan methyl ester (63229-68-5,73327-10-3,84094-71-3) → (6S,10S)-(-)-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indole-8-carboxylate (197143-14-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / TFA / CH₂Cl₂ / 72 h / 20 °C

2: 88 percent / NaH / toluene; methanol / 72 h / Heating

With sodium hydride; trifluoroacetic acid; In methanol; dichloromethane; toluene; 1: Condensation / 2: Cyclization;

DOI:10.1021/jo000126e

Reference yield:

methyl 4,4-dimethoxybutanoate (4220-66-0) → (6S,10S)-(-)-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indole-8-carboxylate (197143-14-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / TFA / CH₂Cl₂ / 72 h / 20 °C

2: 88 percent / NaH / toluene; methanol / 72 h / Heating

With sodium hydride; trifluoroacetic acid; In methanol; dichloromethane; toluene; 1: Condensation / 2: Cyclization;

DOI:10.1021/jo000126e

upstream raw materials:

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

methyl 4,4-dimethoxybutanoate

benzaldehyde

D-(+)-N_bbenzyltryptophan methyl ester

Downstream raw materials:

(6S,10S)-9-(1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole

(6S,10S)-(-)-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole

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

(6S,10S)-(-)-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole

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