(6S,10S,8E)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooctindole-9-carbaldehyde

Base Information

• Chemical Name: (6S,10S,8E)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooctindole-9-carbaldehyde
• CAS No.: 143120-74-5
• Molecular Formula: C₂₃H₂₂N₂O
• Molecular Weight: 342.44

Synonyms:(6S,10S,8E)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooctindole-9-carbaldehyde

Chemical Property of (6S,10S,8E)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooctindole-9-carbaldehyde

Chemical Property:

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Technology Process of (6S,10S,8E)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooctindole-9-carbaldehyde

There total 24 articles about (6S,10S,8E)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooctindole-9-carbaldehyde 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: 99.0%

(6S,10S,8E)-12-Benzyl-9-cyano-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooct[b]indole (157402-88-5) → (6S,10S,8E)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooctindole-9-carbaldehyde (143120-74-5)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;

DOI:10.1039/c39940001559

Reference yield: 80.0%

2'-phenylsulfinyl-5-methyl-12-benzyl-6,7,8,9,10,11-hexahydro-oxirano-spiro<2',9>-6,10-imino-5H-cyclooctindole (122490-83-9,122565-45-1,141847-53-2) → 5-methyl-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole (122490-84-0,143120-74-5)

Guidance literature:

With Tributylphosphine oxide; lithium perchlorate; In toluene; for 1h; Heating;

DOI:10.1016/S0040-4020(01)88507-0

Reference yield:

chloromethyl phenyl sulfoxide (7205-94-9) + (6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole (123806-87-1) → (6S,10S,8E)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooctindole-9-carbaldehyde (143120-74-5)

Guidance literature:

With potassium hydroxide; Tributylphosphine oxide; lithium perchlorate; lithium diisopropyl amide; Yield given. Multistep reaction; 2.) toluene, Δ;

DOI:10.1021/ja00043a043

upstream raw materials:

2'-phenylsulfinyl-5-methyl-12-benzyl-6,7,8,9,10,11-hexahydro-oxirano-spiro<2',9>-6,10-imino-5H-cyclooctindole

5-methyl-9-hydroxy-9α-chloro-phenylsulfinylmethyl-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

(+/)-5-Methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

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

Downstream raw materials:

5-methyl-9-hydroxymethyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole

(-)-(6S,10S)-5-methyl-9-(2'-ethyl-1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooct[b]indole

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

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

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