(6S,10S)-5-methyl-8-(pent-2'-enyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indolyl-9-hydroxymethane

Base Information

• Chemical Name: (6S,10S)-5-methyl-8-(pent-2'-enyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indolyl-9-hydroxymethane
• CAS No.: 219584-02-8
• Molecular Formula: C₂₈H₃₄N₂O
• Molecular Weight: 414.591

Synonyms:(6S,10S)-5-methyl-8-(pent-2'-enyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indolyl-9-hydroxymethane

Chemical Property of (6S,10S)-5-methyl-8-(pent-2'-enyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indolyl-9-hydroxymethane

Chemical Property:

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Technology Process of (6S,10S)-5-methyl-8-(pent-2'-enyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indolyl-9-hydroxymethane

There total 4 articles about (6S,10S)-5-methyl-8-(pent-2'-enyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indolyl-9-hydroxymethane 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: 96.0%

(6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde (219583-98-9) → (6S,10S)-5-methyl-8-(pent-2'-enyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indolyl-9-hydroxymethane (219584-02-8)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jo981815h

Reference yield:

(E)-1-bromo-2-pentene (7348-71-2) → (6S,10S)-5-methyl-8-(pent-2'-enyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indolyl-9-hydroxymethane (219584-02-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / Li; biphenyl; BaI₂ / tetrahydrofuran / -78 °C

2.1: KH; 18-crown-6 / dioxane / 14 h / 100 °C

2.2: 85 percent / methanol / 6 h / 20 °C

3.1: 95 percent / NaH / tetrahydrofuran / 8 h / 0 - 20 °C

4.1: 95 percent / NaBH₄ / methanol / 1 h / 20 °C

With sodium tetrahydroborate; 18-crown-6 ether; biphenyl; barium(II) iodide; lithium; potassium hydride; sodium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; 1.1: Addition / 2.1: Rearrangement / 2.2: epimerization / 3.1: Methylation / 4.1: Reduction;

DOI:10.1021/jo000126e

Reference yield:

(6S,10S)-9-(1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole (217448-25-4) → (6S,10S)-5-methyl-8-(pent-2'-enyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indolyl-9-hydroxymethane (219584-02-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: KH; 18-crown-6 / dioxane / 14 h / 100 °C

1.2: 85 percent / methanol / 6 h / 20 °C

2.1: 95 percent / NaH / tetrahydrofuran / 8 h / 0 - 20 °C

3.1: 95 percent / NaBH₄ / methanol / 1 h / 20 °C

With sodium tetrahydroborate; 18-crown-6 ether; potassium hydride; sodium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; 1.1: Rearrangement / 1.2: epimerization / 2.1: Methylation / 3.1: Reduction;

DOI:10.1021/jo000126e

upstream raw materials:

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

(E)-1-bromo-2-pentene

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

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

Downstream raw materials:

C₂₇H₃₂N₂O₂

C₂₇H₃₀N₂O

C₂₈H₃₂N₂O₂

N_b-benzyl, N_b-21-secotalpinine

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