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

Base Information

• Chemical Name: (6S,10S)-9-(1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole
• CAS No.: 217448-25-4
• Molecular Formula: C₂₇H₃₀N₂O
• Molecular Weight: 398.548

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

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

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of (6S,10S)-9-(1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole

There total 14 articles about (6S,10S)-9-(1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole 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: 90.0%

(E)-1-bromo-2-pentene (7348-71-2) + (6S,10S)-(-)-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole (217448-24-3) → (6S,10S)-9-(1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole (217448-25-4)

Guidance literature:

With biphenyl; barium(II) iodide; lithium; barium; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(98)01788-2

Reference yield:

(6S,10S)-(-)-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole (197143-13-8) → (6S,10S)-9-(1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole (217448-25-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran / -78 °C

1.2: KOH / tetrahydrofuran; H₂O / 20 °C

1.3: 87 percent / LiClO₄ / dioxane / 24 h / Heating

2.1: 90 percent / Li; biphenyl; BaI₂ / tetrahydrofuran / -78 °C

With biphenyl; barium(II) iodide; lithium; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo030116o

Reference yield:

(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-(1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole (217448-25-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 88 percent / NaH / toluene; methanol / 72 h / Heating

2.1: 91 percent / HCl / acetic acid; H₂O / 8 h / Heating

3.1: LDA / tetrahydrofuran

3.2: KOH / tetrahydrofuran; H₂O / 10 h / 20 °C

3.3: 90 percent / LiClO₄ / dioxane / 4 h / Heating

4.1: 90 percent / Li; biphenyl; BaI₂ / tetrahydrofuran / -78 °C

With hydrogenchloride; biphenyl; barium(II) iodide; lithium; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; water; acetic acid; toluene; 1.1: Cyclization / 2.1: Decarboxylation / 3.1: Alkylation / 3.2: Hydrolysis / 3.3: Oxidation / 4.1: Addition;

DOI:10.1021/jo000126e

upstream raw materials:

(E)-1-bromo-2-pentene

(6S,10S)-(-)-9-formyl-12-benzyl-6,7,10,11-tetrahydro-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

benzaldehyde

Downstream raw materials:

(6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde

(6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde

(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-oxomethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]-indole

(6S,9S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]-indolyl-9-acetal

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