Synthesis of 1-azabicyclo[3.2.2]nonane from cinchonidine

Abstract

The 1-azabicyclo[3.2.2]nonane is a potent building block which have important bio­logicaly activities including for Alzheimer and ashmatic treatment. The skeleton can be accessed by rearrangement of quinuclidine ring in Cinchona alkaloids. The rearrange­ment established three chiral center at C-2, C-3, and C-6. The rearrangement of qui­nuclidine moiety to azabicyclic[3.2.2]nonana system of mesylated cinchonidine took place by hydrolysis in a mixture of acetone–water (1:1) with 47% yields. The structure determination of the product and its absolute configuration of chiral centers were esta­blished by using spectroscopy data including, 1H NMR, 13C NMR, 1D NOE and HR-MS.