210165-71-2

Upstream product

• 3612-20-2 1-phenylmethyl-4-piperidone 
• 124-02-7 diallylamine 
• 210165-68-7 Diallyl-(1-benzyl-3-chloro-1,2,3,6-tetrahydro-pyridin-4-yl)-amine 
• 210165-67-6 Diallyl-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-amine 
• 210307-06-5 1α,5α,6β-3-benzyl-6-diallylamino-3-azabicyclo[3.1.0]hexane-6-carbonitrile 
• 210165-69-8 Diallyl-((1R,5S,6S)-3-benzyl-6-methoxy-3-aza-bicyclo[3.1.0]hex-6-yl)-amine 

Downstream Products

• 210236-56-9 (1α,5α,6α)-3-benzyl-3-azabicyclo [3.1.0]-6-amino hexane 

Relevant academic research and scientific papers

Diastereoselective syntheses of N-protected derivatives of 1α,5α,6β- 6-amino-3-azabicyclo[3.1.0]hexane; a route to trovafloxacin 6β-diastereomer

N-Protected derivatives 12, 13 and 17 of 1α,5α,6β-6-amino-3- azabicyclo[3.1.0]hexane 5 were synthesized via chloroenamines 6a or 6b. The specific N-protection was realized either by using a chloroenamine 6b with different protecting groups or by selective removal of identical protecting groups at the bicyclic target molecule 7. Dibenzylamino compound 13 allowed the preparation of naphthyridine derivative 25 which represents the 6β- diastereomer of trovafloxacin mesylate, a potent Gyrase inhibitor.

Reductive decyanation of N-protected 6-amino-3-aza-bicyclo [3.1.0]hexanecarbonitriles

The cyano moiety in dibenzylamino-3-azabicyclo[3.1.0]hexane-6- carbonitriles 14c,d can be removed reductively by alkali metals: sodium in liquid ammonia at low temperatures causes a reaction with retention of configuration whilst lithium in an ethylamine - ammonia mixture at 0°C leads predominantly to inversion of configuration. The analogous diallylamino species 14e is less suitable for reductive decyanation. It can be used, however, for the synthesis of a 3-azabicyclo[3.2.0]heptane diamine 22. The solid state conformation of an N(3)-unsubstituted 3-azabicyclohexane skeleton is determined by an X-ray structural analysis.