3-Azabicyclo[3.1.0]hexane-3-carboxylic acid, 6,6-dibromo-, phenylmethyl ester

Base Information

• Chemical Name: 3-Azabicyclo[3.1.0]hexane-3-carboxylic acid, 6,6-dibromo-, phenylmethyl ester
• CAS No.: 681425-42-3
• Molecular Formula: C13H13Br2NO2
• Molecular Weight: 375.06
• Mol file: 681425-42-3.mol

Synonyms:benzyl 6,6-dibromo-3-azabicyclo[3.1.0]hexane-3-carboxylate;6,6-Dibromo-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester;

Chemical Property of 3-Azabicyclo[3.1.0]hexane-3-carboxylic acid, 6,6-dibromo-, phenylmethyl ester

Chemical Property:

• PSA: 29.54000
• LogP: 3.30880

Purity/Quality:

97% ^*data from raw suppliers

3-Cbz-6,6-dibromo-3-azabicyclo[3.1.0]hexane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Azabicyclo[3.1.0]hexane-3-carboxylic acid, 6,6-dibromo-, phenylmethyl ester

There total 1 articles about 3-Azabicyclo[3.1.0]hexane-3-carboxylic acid, 6,6-dibromo-, phenylmethyl 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: 54.0%

1-carboxybenzyl-3-pyrrolidine (31970-04-4) + Bromoform (75-25-2) → 6,6-dibromo-3-azabicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester (681425-42-3)

Guidance literature:

With 15-crown-5; N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In dichloromethane;

Reference yield: 24.0%

6,6-dibromo-3-azabicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester (681425-42-3) → benzyl 6-hydroxy-3-azabicyclo[3.1.0]hexane-3-carboxylate (1255099-53-6)

Guidance literature:

6,6-dibromo-3-azabicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester; With n-butyllithium; benzo[1,3,2]dioxaborole; In tetrahydrofuran; hexane; at 20 - 50 ℃; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; hexane; at 0 ℃; Inert atmosphere;

Reference yield: 15.0%

6,6-dibromo-3-azabicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester (681425-42-3) → (1α,5α,6α)-6-hydroxy-3-azabicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester (504438-12-4,1255099-53-6)

Guidance literature:

6,6-dibromo-3-azabicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester; With n-butyllithium; In tetrahydrofuran; at -95 ℃; for 0.166667h;

With benzo[1,3,2]dioxaborole; In tetrahydrofuran; at 50 ℃; for 16h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; for 18h;

DOI:10.1021/jm058204j

upstream raw materials:

1-carboxybenzyl-3-pyrrolidine

Bromoform

Downstream raw materials:

(1α,5α,6α)-6-hydroxy-3-azabicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

(1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexan-1-ol

4-[(1S,5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-aza-bicyclo[3.1.0]hex-3-yl]-3,5-difluoro-phenylamine

(1α,5α,6α)-6-(tert-butyldimethylsilyloxy)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexane