(3aS,6aR,11bR)-3,7-Dibenzyl-3a-hydroxy-3a,4,5,6,6a,7-hexahydro-3H-pyrrolo[2,3-d]carbazol-2-one

Base Information

• Chemical Name: (3aS,6aR,11bR)-3,7-Dibenzyl-3a-hydroxy-3a,4,5,6,6a,7-hexahydro-3H-pyrrolo[2,3-d]carbazol-2-one
• CAS No.: 129593-02-8
• Molecular Formula: C₂₈H₂₈N₂O₂
• Molecular Weight: 424.543
• Mol file: 129593-02-8.mol

Synonyms:(3aS,6aR,11bR)-3,7-Dibenzyl-3a-hydroxy-3a,4,5,6,6a,7-hexahydro-3H-pyrrolo[2,3-d]carbazol-2-one

Chemical Property of (3aS,6aR,11bR)-3,7-Dibenzyl-3a-hydroxy-3a,4,5,6,6a,7-hexahydro-3H-pyrrolo[2,3-d]carbazol-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,6aR,11bR)-3,7-Dibenzyl-3a-hydroxy-3a,4,5,6,6a,7-hexahydro-3H-pyrrolo[2,3-d]carbazol-2-one

There total 1 articles about (3aS,6aR,11bR)-3,7-Dibenzyl-3a-hydroxy-3a,4,5,6,6a,7-hexahydro-3H-pyrrolo[2,3-d]carbazol-2-one 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:

N-(iodoacetyl)benzylamine (64297-96-7) + 9-benzyl-1,2,3,4a,9,9a-hexahydrocarbazol-4-one (99459-02-6,117290-75-2,117290-84-3) → (3aS,6aR,11bR)-3,7-Dibenzyl-3a-hydroxy-3a,4,5,6,6a,7-hexahydro-3H-pyrrolo[2,3-d]carbazol-2-one (129593-02-8)

Guidance literature:

With potassium hydride; Yield given. Multistep reaction; 1) THF, 5 min, r.t., 2) 10 min;

DOI:10.1021/jo00307a019

Reference yield: 59.0%

(3aS,6aR,11bR)-3,7-Dibenzyl-3a-hydroxy-3a,4,5,6,6a,7-hexahydro-3H-pyrrolo[2,3-d]carbazol-2-one (129593-02-8) → (6aS,11bS)-3-Benzyl-5,6,6a,7-tetrahydro-3H-pyrrolo[2,3-d]carbazol-2-one (129593-04-0) + (3aR,6aS,11bS)-3-Benzyl-3a-hydroxy-3a,4,5,6,6a,7-hexahydro-3H-pyrrolo[2,3-d]carbazol-2-one (129593-03-9)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; chloroform; for 20h; under 2585.7 Torr; Ambient temperature;

DOI:10.1021/jo00307a019

Reference yield:

(3aS,6aR,11bR)-3,7-Dibenzyl-3a-hydroxy-3a,4,5,6,6a,7-hexahydro-3H-pyrrolo[2,3-d]carbazol-2-one (129593-02-8) → 1-((3aR,4S,6aR,11bR)-7-Acetyl-3-benzyl-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo[2,3-d]carbazol-4-yl)-ethanone (129593-07-3,129704-18-3,129704-19-4,129704-24-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 40 percent / conc. HCl, H₂ / 10percent Pd/C / CHCl₃; ethanol / 20 h / 2585.7 Torr / Ambient temperature

2: LiAlH₄ / tetrahydrofuran / 12 h / Heating

3: 75 percent / triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

4: 1) trimethyloxonium tetrafluoroborate, 2) sodium borohydride / 1) CH₂Cl₂, 0 deg C, 2) CH₃OH, 0 deg C; 80percent, only isomer

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; trimethoxonium tetrafluoroborate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform;

DOI:10.1021/jo00307a019

upstream raw materials:

N-(iodoacetyl)benzylamine

9-benzyl-1,2,3,4a,9,9a-hexahydrocarbazol-4-one

Downstream raw materials:

(6aS,11bS)-3-Benzyl-5,6,6a,7-tetrahydro-3H-pyrrolo[2,3-d]carbazol-2-one

(3aR,6aS,11bS)-3-Benzyl-3a-hydroxy-3a,4,5,6,6a,7-hexahydro-3H-pyrrolo[2,3-d]carbazol-2-one

(6aS,11bS)-3-Benzyl-2,3,5,6,6a,7-hexahydro-1H-pyrrolo[2,3-d]carbazole

(3aR,10bR,12bR)-1-(2,3,4,5,11,12-Hexahydro-1H-6,12a-diaza-indeno[7,1-cd]fluoren-3a-yl)-ethanone