3-Azabicyclo[3.1.0]hexane-3-carboxylicacid,6-amino-,1,1-dimethylethylester,

Base Information

• Chemical Name: 3-Azabicyclo[3.1.0]hexane-3-carboxylicacid,6-amino-,1,1-dimethylethylester,
• CAS No.: 273206-92-1
• Molecular Formula: C10H18N2O2
• Molecular Weight: 198.26
• Hs Code.: 2933990090
• Mol file: 273206-92-1.mol

Synonyms:trans-tert-butyl 6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate;exo-6-Amino-3-Boc-3-azabicyclo[3.1.0]hexane;exo-6-Amino-3-Boc-3-azabi...;

Chemical Property of 3-Azabicyclo[3.1.0]hexane-3-carboxylicacid,6-amino-,1,1-dimethylethylester,

Chemical Property:

• Vapor Pressure: 0.000827mmHg at 25°C
• Boiling Point: 275℃
• PKA: 8.52±0.20(Predicted)
• Flash Point: 120℃
• PSA: 55.56000
• Density: 1.144
• LogP: 1.44860
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1α,5α,6α)-6-Amino-3-azabicyclo[3.1.0]hexane-3-carboxylicAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (1α,5α,6α)-6-Amino-3-azabicyclo[3.1.0]hexane-3-carboxylic Acid 1,1-Dimethylethyl Ester, is an intermediate in the preparation of a novel series of Histone Deacetylase (HDAC) Inhibitors, demonstrating class I selectivity and good oral bioavailability. It can also be used in the synthesis of Alatrofloxacin Mesylate (A511400).

Technology Process of 3-Azabicyclo[3.1.0]hexane-3-carboxylicacid,6-amino-,1,1-dimethylethylester,

There total 10 articles about 3-Azabicyclo[3.1.0]hexane-3-carboxylicacid,6-amino-,1,1-dimethylethylester, 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: 98.0%

tert-butyl (1R,5S,6s)-6-(N,N-dibenzylamino)-3-azabicyclo[3.1.0]hexane-3-carboxylate (497163-57-2) → tert-butyl (1S,3R,5R)-6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate (2256715-14-5,273206-92-1,1453252-65-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 12h;

DOI:10.1002/1521-3765(20020816)8:16<3789::AID-CHEM3789>3.0.CO;2-R

Reference yield: 95.0%

tert-butyl 6-nitro-3-azabicyclo[3.1.0]hexane-3-carboxylate (914937-14-7) → 6-amino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (208837-83-6,2256715-14-5,273206-92-1,1453252-65-7)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In ethanol; for 18h;

Reference yield: 95.0%

tert-butyl 6-nitro-3-azabicyclo[3.1.0]hexane-3-carboxylate (1256448-51-7) → (1s,5r)-6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (2256715-14-5,273206-92-1,1453252-65-7)

Guidance literature:

With 10% palladium on activated carbon; hydrogen; In ethanol; at 20 ℃; for 18h;

DOI:10.1021/jm101177s

upstream raw materials:

tert-butyl (1R,5S,6s)-6-(N,N-dibenzylamino)-3-azabicyclo[3.1.0]hexane-3-carboxylate

N-(tert-butoxycarbonyl)-3-pyrroline

tert-butyl 6-nitro-3-azabicyclo[3.1.0]hexane-3-carboxylate

(1α,5α,6α)-3-N-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane

Downstream raw materials:

tert-butyl (2R,5S)-6-(methylamino)-3-azabicyclo[3.1.0]hexane-3-carboxylate

N-3-aza-bicyclo[3.1.0]hex-6-yl-4-{[(4-ethoxybenzenesulfonyl)pyridin-2-ylmethylamino]methyl}benzamide

Refernces

• 1、 Moffat, David,Patel, Sanjay,Day, Francesca,Belfield, Andrew,Donald, Alastair,Rowlands, Martin,Wibawa, Judata,Brotherton, Deborah,Stimson, Lindsay,Clark, Vanessa,Owen, Jo,Bawden, Lindsay,Box, Gary,Bone, Elisabeth,Mortenson, Paul,Hardcastle, Anthea,Van Meurs, Sandra,Eccles, Suzanne,Raynaud, Florence,Aherne, Wynne. "Discovery of 2-(6-{[(6-Fluoroquinolin-2-yl)methyl]amino}bicyclo[3.1.0]hex- 3-yl)- N -hydroxypyrimidine-5-carboxamide (CHR-3996), a class i selective orally active histone deacetylase inhibitor". experimental part. p. 8663 - 8678. Retrieved 2011/03/19.
• 2、 -. "HISTONE DEACETYLASE INHIBITORS". Page/Page column 18; 29. . Retrieved 2010/11/25.