(-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-pentenyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

Base Information

• Chemical Name: (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-pentenyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole
• CAS No.: 143065-02-5
• Molecular Formula: C₃₂H₄₀N₂O₂
• Molecular Weight: 484.682

Synonyms:(-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-pentenyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

Chemical Property of (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-pentenyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

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Technology Process of (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-pentenyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

There total 7 articles about (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-pentenyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole 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: 92.0%

ethylene glycol (107-21-1) + (-)-(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 (143065-00-3) → (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-pentenyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (143065-02-5)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 3h; Heating;

DOI:10.1021/jo00055a019

Reference yield:

3-bromo-4-heptene (143064-98-6) → (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-pentenyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (143065-02-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) magnesium / 1) THF, 2) 0 deg C, 2 h

2: KH, 18-crown-6 ether / dioxane / a) r.t., 2 h, b) cumene, reflux, 14 h

3: 92 percent / pTSA / benzene / 3 h / Heating

With 18-crown-6 ether; potassium hydride; toluene-4-sulfonic acid; magnesium; In 1,4-dioxane; benzene;

DOI:10.1021/jo00055a019

Reference yield:

(6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole (123806-87-1) → (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-pentenyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (143065-02-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LDA, KOH, 2.) LiClO4, n-Bu3PO / 2.) toluene, Δ

2: Mg / tetrahydrofuran / 0 °C

3: KH, 18-crown-6 / dioxane; various solvent(s) / 150 °C

4: 90 percent / pTSA / benzene / Heating

With potassium hydroxide; 18-crown-6 ether; Tributylphosphine oxide; lithium perchlorate; potassium hydride; toluene-4-sulfonic acid; magnesium; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; benzene;

DOI:10.1021/ja00043a043

upstream raw materials:

ethylene glycol

(-)-(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

trans-2-pentenal

(+/-)-(E)-hept-4-en-3-ol

Downstream raw materials:

(-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-hydroxyethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

(-)-N_b-benzylraumacline

(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

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