(6R,10R)-(+)-5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

Base Information

• Chemical Name: (6R,10R)-(+)-5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole
• CAS No.: 129708-76-5
• Molecular Formula: C₂₈H₂₆N₂O
• Molecular Weight: 406.527
• Mol file: 129708-76-5.mol

Synonyms:(6R,10R)-(+)-5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

Chemical Property of (6R,10R)-(+)-5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,10R)-(+)-5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

There total 16 articles about (6R,10R)-(+)-5,12-dibenzyl-9-oxo-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: 99.0%

(6R,10R)-(+)-methyl 5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-8-carboxylate (119184-23-5,119241-71-3) → (6R,10R)-(+)-5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (129708-76-5)

Guidance literature:

With sulfuric acid; acetic acid; In water; for 72h; Heating;

DOI:10.1021/ja00169a033

Reference yield: 70.0%

(endo)-5,12-Dibenzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indol-9-ol → (6R,10R)-(+)-5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (129708-76-5)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 - 20 ℃; for 0.366667h;

DOI:10.1055/s-2000-6350

Reference yield:

(S)-3-(1-Benzyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester (129708-73-2) → (6R,10R)-(+)-5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (129708-76-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / sodium borohydride / methanol / 1 h / 25 °C

2: 67 percent / benzene; dioxane / 24 h / Heating

3: chlorotrimethylsilane / 25 °C

4: 72 percent / NaH, MeOH / toluene / 16 h / Heating

5: 99 percent / HOAc, H₂SO₄ / H₂O / 72 h / Heating

With methanol; sodium tetrahydroborate; chloro-trimethyl-silane; sulfuric acid; sodium hydride; acetic acid; In 1,4-dioxane; methanol; water; toluene; benzene;

DOI:10.1021/ja00169a033

upstream raw materials:

(6R,10R)-(+)-methyl 5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-8-carboxylate

benzoyl chloride

(S)-3-(1-Benzyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester

(S)-(-)-N,N'-dibenzyltryptophan methyl ester

Downstream raw materials:

(E)-(+)-(16S)-12-benzyl-10-desoxy-18-oxo-18-methoxysarpagine

(Z)-(+)-(16S)-12-benzyl-10-desoxy-18-oxo-18-methoxysarpagine

(E)-(+)-(16S)-12-benzyl-10-desoxy-18-hydroxysarpagine

(Z)-(+)-(16S)-12-benzyl-10-desoxy-18-hydroxysarpagine