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

Base Information

• Chemical Name: (6S,10S)-(-)-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole
• CAS No.: 197143-13-8
• Molecular Formula: C₂₁H₂₀N₂O
• Molecular Weight: 316.403

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

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

Chemical Property:

Purity/Quality:

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

There total 13 articles about (6S,10S)-(-)-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[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: 91.0%

(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) → (6S,10S)-(-)-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole (197143-13-8)

Guidance literature:

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

DOI:10.1021/jo000126e

Reference yield: 82.0%

(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)-(-)-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole (197143-13-8)

Guidance literature:

(1S,3R)-(-)-methyl 2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate; With sodium hydride; In methanol; toluene; mineral oil; at 23 ℃; for 72.5h; Dean-Stark; Inert atmosphere; Reflux;

With hydrogenchloride; acetic acid; In water; for 8h; Reflux; Inert atmosphere;

DOI:10.1002/chem.201703572

Reference yield:

D-(+)-Nbbenzyltryptophan methyl ester (63229-68-5,73327-10-3,84094-71-3) → (6S,10S)-(-)-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole (197143-13-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 400 g / CF₃COOH / methanol; CH₂Cl₂ / 240 h / 20 °C

2.1: NaH / methanol; toluene / 72 h / Heating

2.2: 80 percent / CH₃COOH; HCl / methanol; toluene; H₂O / 10 h / Heating

With sodium hydride; trifluoroacetic acid; In methanol; dichloromethane; toluene; 1.1: Pictet-Spengler reaction / 2.1: Dieckmann cyclization;

DOI:10.1021/jo030006h

upstream raw materials:

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

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

benzaldehyde

D-(+)-N_bbenzyltryptophan methyl ester

Downstream raw materials:

C₂₈H₂₆N₂O₂S

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

(+)-3-ethylidene-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methanoindolo[2,3-a]quinolizine-13-carboxaldehyde

C₂₁H₂₀N₂O₂

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