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■ A Stereoselective Synthesis of cis-4-Acetonyl-1-benzyl-3-ethylpiperidine

Josep Bonjoch, Ana Linares, Manel Guardià, and Joan Bosch

*Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Av. de Joan XXIII, s/n, 08028 Barcelona, Spain

Abstract

The title compound cis-1, a potential synthon for indole alkaloid synthesis, is prepared for the first time. The synthesis starts with the condensation of 3-ethyl-4-piperidone 2 with triethyl phosphonoacetate followed by stereoselective hydrogenation of the resulting α,β-unsaturated ester 5 to give 4-piperidineacetate cis - 6 as the major isomer. This was converted in high yield to the target molecule cis-1 by a two-step sequence through the corresponding β-keto sulfoxide cis-7.