(1R,5S,6s)-3-benzyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate

Base Information

• Chemical Name: (1R,5S,6s)-3-benzyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate
• CAS No.: 134575-38-5
• Molecular Formula: C16H19NO4
• Molecular Weight: 289.331
• Mol file: 134575-38-5.mol

Synonyms:[1α,5α,6β]-3-benzyloxycarbonyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid,ethyl ester;3-benzyl 6-ethyl (1R,5S,6s)-3-azabicyclo3.1.0hexane-3,6-dicarboxylate;(1α,5α,6β)-3-aza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid 3-benzyl ester 6-ethyl ester;[1α,5α,6β]-3-benzyloxycarbonyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid, ethyl ester;(1S,5R,6S)-3-Aza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid 3-benzyl ester 6-ethyl ester;

Chemical Property of (1R,5S,6s)-3-benzyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate

Chemical Property:

• PSA: 55.84000
• LogP: 2.00200

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S,6s)-3-benzyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate

There total 4 articles about (1R,5S,6s)-3-benzyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate 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: 35.0%

diazoacetic acid ethyl ester (623-73-4) + 1-carboxybenzyl-3-pyrrolidine (31970-04-4) → 3-benzyl 6-ethyl (1α,5α,6β)-3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate (134575-38-5) + 3-benzyl 6-ethyl (1α,5α,6α)-3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate (146726-10-5)

Guidance literature:

With dirhodium tetraacetate; In 1,2-dichloro-ethane; at 80 ℃; for 5h;

Reference yield: 28.0%

1-carboxybenzyl-3-pyrrolidine (31970-04-4) → 3-benzyl 6-ethyl (1α,5α,6β)-3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate (134575-38-5) + 3-benzyl 6-ethyl (1α,5α,6α)-3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate (146726-10-5)

Guidance literature:

rhodium(II) acetate; In hexane; dichloromethane; ethyl acetate;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → 3-benzyl 6-ethyl (1α,5α,6β)-3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate (134575-38-5)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 14 h / 0 - 20 °C

2: dirhodium tetraacetate / 1,2-dichloro-ethane / 5 h / 80 °C

With dirhodium tetraacetate; In dichloromethane; 1,2-dichloro-ethane;

upstream raw materials:

diazoacetic acid ethyl ester

1-carboxybenzyl-3-pyrrolidine

benzyl chloroformate

Downstream raw materials:

[1α,5α,6β]-3-Benzyloxycarbonyl-3-azabicyclo[3.1.0] hexane-6-carboxylic acid

[(1α,5α,6β)-3-(4-benzyloxycarbonylamino-2,6-difluorophenyl)-3-azabicyclo[3.1.0]hex-6-yl]carbamic acid tert-butyl ester

[endo-(1R,5S)-3-(2,6-difluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-yl]carbamic acid tert-butyl ester

[(1R,5S,6R)-3-(4-Amino-2,6-difluoro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-yl]-carbamic acid tert-butyl ester