(6S,10S)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-5H-6,10-iminocycloocta[b]indole-9-carbaldehyde ethylene acetal

Base Information

• Chemical Name: (6S,10S)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-5H-6,10-iminocycloocta[b]indole-9-carbaldehyde ethylene acetal
• CAS No.: 318269-63-5
• Molecular Formula: C₂₅H₂₆N₂O₂
• Molecular Weight: 386.494

Synonyms:(6S,10S)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-5H-6,10-iminocycloocta[b]indole-9-carbaldehyde ethylene acetal

Chemical Property of (6S,10S)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-5H-6,10-iminocycloocta[b]indole-9-carbaldehyde ethylene acetal

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Technology Process of (6S,10S)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-5H-6,10-iminocycloocta[b]indole-9-carbaldehyde ethylene acetal

There total 4 articles about (6S,10S)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-5H-6,10-iminocycloocta[b]indole-9-carbaldehyde ethylene acetal 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: 89.0%

ethylene glycol (107-21-1) + (6S,10S,8E)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooctindole-9-carbaldehyde (143120-74-5) → (6S,10S)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-5H-6,10-iminocycloocta[b]indole-9-carbaldehyde ethylene acetal (318269-63-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1039/b005694o

Reference yield: 65.0%

ethylene glycol (107-21-1) + (6S,8S,9R,10S)-12-Benzyl-8-tert-butyldimethylsilyloxy-5-methyl-6,7,8,9,10,11-hexahydro-5H-6,10-iminocycloocta[b]indole-9-carbaldehyde → (6S,10S)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-5H-6,10-iminocycloocta[b]indole-9-carbaldehyde ethylene acetal (318269-63-5)

Guidance literature:

With toluene-4-sulfonic acid; for 2h; Heating;

DOI:10.1039/b005694o

Reference yield:

C23H23N3O → (6S,10S)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-5H-6,10-iminocycloocta[b]indole-9-carbaldehyde ethylene acetal (318269-63-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / 2,6-dimethylpyridine / CH₂Cl₂ / 24 h / 20 °C

2: 85 percent / DIBAL-H / CH₂Cl₂ / 2.5 h / -78 - 20 °C

3: 65 percent / PTSA / 2 h / Heating

With 2,6-dimethylpyridine; diisobutylaluminium hydride; toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1039/b005694o

upstream raw materials:

ethylene glycol

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

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