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

Base Information

• Chemical Name: Phenyl-carbamic acid (3aR,8aS)-8-benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester
• CAS No.: 193604-51-2
• Molecular Formula: C₂₆H₂₇N₃O₂
• Molecular Weight: 413.519
• Mol file: 193604-51-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about Phenyl-carbamic acid (3aR,8aS)-8-benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester 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:

2-(5-methoxyindol-3-yl)ethylamine (608-07-1) → Phenyl-carbamic acid (3aR,8aS)-8-benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester (193604-51-2)

Guidance literature:

Multi-step reaction with 8 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: 91.1 percent / BBr₃ / CHCl₃ / 4 h / Ambient temperature

8: 73.7 percent / Na / diethyl ether / Ambient temperature

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

DOI:10.1021/jm970210v

Reference yield:

methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate (67199-10-4) → Phenyl-carbamic acid (3aR,8aS)-8-benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester (193604-51-2)

Guidance literature:

Multi-step reaction with 7 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: 91.1 percent / BBr₃ / CHCl₃ / 4 h / Ambient temperature

7: 73.7 percent / Na / diethyl ether / Ambient temperature

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

DOI:10.1021/jm970210v

Reference yield:

[2-(1-Benzyl-5-methoxy-1H-indol-3-yl)-ethyl]-carbamic acid methyl ester (193604-37-4) → Phenyl-carbamic acid (3aR,8aS)-8-benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester (193604-51-2)

Guidance literature:

Multi-step reaction with 6 steps

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

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

3: 75.3 percent / Red-Al / benzene / 5 h / Ambient temperature

5: 91.1 percent / BBr₃ / CHCl₃ / 4 h / Ambient temperature

6: 73.7 percent / Na / diethyl ether / Ambient temperature

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

DOI:10.1021/jm970210v

upstream raw materials:

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

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

Refernces