2256715-14-5

Basic information

• Product Name: 6-amino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester
• CAS NO: 2256715-14-5
• Molecular Weight: 198.265
• Mol File: 2256715-14-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 6-amino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 6-amino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester(2256715-14-5)
• EPA Substance Registry System: 6-amino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester(2256715-14-5)

Safety Data

• Hazardous Substances Data: 2256715-14-5(Hazardous Substances Data)

Upstream product

• 914937-14-7 tert-butyl 6-nitro-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 497163-57-2 tert-butyl (1R,5S,6s)-6-(N,N-dibenzylamino)-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 73286-70-1 N-(tert-butoxycarbonyl)-3-pyrroline 
• 151860-15-0 (1α,5α,6α)-3-N-benzyl-6-nitro-2,4-dioxo-3-azabicyclo[3.1.0]hexane 
• 151860-16-1 (1α,5α,6α)-3-N-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane 
• 1256448-51-7 tert-butyl 6-nitro-3-azabicyclo[3.1.0]hexane-3-carboxylate 

Downstream Products

• 1352926-02-3 tert-butyl (2R,5S)-6-(methylamino)-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 1003946-86-8 (1R_.5S_.6s)-tert-butyl 6-(((benzyloxy)carbonyl)amino)-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 1612172-51-6 (1R_.5S_.6s)-tert-butyl 6-(((benzyloxy)carbonyl)(methyl)amino)-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 1612172-56-1 benzyl N-((1R,5S,6s)-3-(4-((1-isopropyl-1H-imidazo[4,5-c]pyridin-6-yl)amino)pyrimidin-2-yl)-3-azabicyclo[3.1.0]hexan-6-yl)carbamate 
• 1003946-73-3 benzyl (1R,5S,6s)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate 
• 1191068-23-1 N-3-aza-bicyclo[3.1.0]hex-6-yl-4-{[(4-ethoxybenzenesulfonyl)pyridin-2-ylmethylamino]methyl}benzamide 

Relevant articles and documents

Practical Synthesis of a 6-Triazolylazabicyclo[3.1.0]hexane

We describe a practical, scalable synthesis of an advanced heterocyclic intermediate, (1R,5S,6s)-6-(4H-1,2,4-triazol-4-yl)-3-azabicyclo[3.1.0]hexane. A robust synthetic sequence based on a Kulinkovich-de Meijere pyrroline cyclopropanation followed by tran

2-AMINO PYRIDINE COMPOUNDS

The present invention is directed to 2-aminopyrimidine compounds and pharmaceutically acceptable salts thereof, their synthesis and their use as HSP-90 inhibitors.

Mono- and disubstituted N,N-dialkylcyclopropylamines from dialkylformamides via ligand-exchanged titanium - Alkene complexes

Dibenzylformamide was treated with cyclohexylmagnesium bromide in the presence of either titanium tetraisopropoxide or methyltitanium triisopropoxide and a variety of cyclic and acyclic alkenes and alkadienes to give new mono- and disubstituted as well as bicyclic dialkylcyclopropylamines (Tables 1-3) in yields ranging from 18 to 90% (in most cases around 55%). 3-Benzyl-6-(N,N-dibenzylamino)-3-azabicyclo[3.1.0]hexane (10a) and the orthogonally bisprotected 3-tert-butoxycarbonyl-6-(N,N-dibenzyl)- 3-azabicyclo[3.1.0]hexane (10d) as well as the analogous 6-(N,N-dibenzylamino)bicyclo[3.1.0]hexane (12) were obtained as pure exo diastereomers in particularly high yields (87, 90, and 88%, respectively) from N-benzylpyrroline (15a), N-Boc-pyrroline (15d; Boc = tert-butyloxycarbonyl) and cyclopentene (19). 1,3-Butadiene (52) and substituted 1,3-butadienes were also aminocyclopropanated quite well to give 2-ethenylcyclopropylamines in good yields (51-64%). Except for alkenyl and aryl-substituted compounds, N,N-dibenzylcyclopropylamines can be debenzylated by catalytic hydrogenation to the primary cyclopropylamines as demonstrated for 10a and 10d to yield the fully deprotected 10e (93%) and mono-Boc-protected 10f (98%), respectively. The latter are interesting templates for combinatorial syntheses of libraries of small molecules with a well defined distance of 4.3 A between two nitrogen atoms.