Reductive decyanation of N-protected 6-Amino-3-azabicyclo[3.1.0]hexanecarbonitriles

✍ Scribed by Elmar Vilsmaier; Gunther Milch; Uwe Bergsträßer

• Book ID: 104208588
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 627 KB
• Volume: 54
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)00298-1

✦ Synopsis

The cyano moiety in dibenzylamino-3-azabicyclo[3.l.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 fithium 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.