(3aS,8aR)-8-Benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-ol

Base Information

• Chemical Name: (3aS,8aR)-8-Benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-ol
• CAS No.: 193604-42-1
• Molecular Formula: C₁₉H₂₂N₂O
• Molecular Weight: 294.396
• Mol file: 193604-42-1.mol

Synonyms:(3aS,8aR)-8-Benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-ol

Chemical Property of (3aS,8aR)-8-Benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,8aR)-8-Benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-ol

There total 7 articles about (3aS,8aR)-8-Benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-ol 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: 95.5%

(3aS,8aR)-8-Benzyl-5-methoxy-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole (193604-41-0) → (3aS,8aR)-8-Benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-ol (193604-42-1)

Guidance literature:

With boron tribromide; In chloroform; for 4h; Ambient temperature;

DOI:10.1021/jm970210v

Reference yield:

2-(5-methoxyindol-3-yl)ethylamine (608-07-1) → (3aS,8aR)-8-Benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-ol (193604-42-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / Et₃N / CH₂Cl₂ / 0.33 h / Ambient temperature

2: 1.) NaH / 1.) DMSO, RT, 20 min, 2.) DMSO, 2 h

3: 77.5 percent / DMSO, 36percent aq. HCl / 1 h / Ambient temperature

4: 94.9 percent / 20percent aq. NaOH, benzyltrimethylammonium bromide / CH₂Cl₂ / 2 h / Ambient temperature

5: 75.3 percent / Red-Al / benzene / 5 h / Ambient temperature

7: 95.5 percent / BBr₃ / CHCl₃ / 4 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; boron tribromide; trimethylbenzylammonium bromide; sodium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In dichloromethane; chloroform; benzene;

DOI:10.1021/jm970210v

Reference yield:

methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate (67199-10-4) → (3aS,8aR)-8-Benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-ol (193604-42-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH / 1.) DMSO, RT, 20 min, 2.) DMSO, 2 h

2: 77.5 percent / DMSO, 36percent aq. HCl / 1 h / Ambient temperature

3: 94.9 percent / 20percent aq. NaOH, benzyltrimethylammonium bromide / CH₂Cl₂ / 2 h / Ambient temperature

4: 75.3 percent / Red-Al / benzene / 5 h / Ambient temperature

6: 95.5 percent / BBr₃ / CHCl₃ / 4 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; boron tribromide; trimethylbenzylammonium bromide; sodium hydride; dimethyl sulfoxide; sodium bis(2-methoxyethoxy)aluminium dihydride; In dichloromethane; chloroform; benzene;

DOI:10.1021/jm970210v

upstream raw materials:

(3aS,8aR)-8-Benzyl-5-methoxy-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole

2-(5-methoxyindol-3-yl)ethylamine

methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate

[2-(1-Benzyl-5-methoxy-1H-indol-3-yl)-ethyl]-carbamic acid methyl ester

Downstream raw materials:

Methyl-carbamic acid (3aS,8aR)-8-benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester

(-)-norphysostigmine