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Paper | Regular issue | Vol 36, No. 11, 1993, pp.2549-2556
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6480
Synthesis of (±)-2β-Hydroxy-6α-acetoxynortropane

Xue-Feng Pei and Jia-Xiang Shen*

*Laboratory of Medical Chemistry, National Institute of Pharmaceutical Research and Development, P.O.Box 948, Beijing 100083, China


8-Benzyl-6α-chloro-6β-carbonitrile-2,2-ethylenedioxy-8-azabicyclo[3.2.1]oct-3-ene (8) and its C(6) epimer (9) were hydrolyzed to afford 6-ketone (10). Reduction of the ketone (10) with sodium borohydride gave predominantly 6α-ol (14). 2-Ketone (20), obtained from 14 by deprotection followed by hydrogenation and acetylation, was reduced with sodium borohydride to give 2β-ol 21 as the major epimer. Nortropane (24) was prepared from 21 by debenzylation.