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Communication | Regular issue | Vol 34, No. 4, 1992, pp.679-684
Published online, 1st January, 1970
DOI: 10.3987/COM-92-5984
Preparation of (1R,4R)-1-Methyl-2-(p-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo[2.2.1]heptane, Intermediate in a Synthesis of New Naphthyridones

Philippe Remuzon,* Massoud Massoudi, Daniel Bouzard, and Jean-Pierre Jacquet

*Bristol-Myers Squibb Pharmaceutical Research Institute, BP 62, Lognes, 77422 Marne-la-Vallee Cedex 2, France

Abstract

An efficient chiral synthesis of the (1R,4R)-1-methyl-2-(p-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo[2.2.1]heptane (2b) was performed using trans-4-hydroxy-L-proline as starting material. This bridged piperazine was used in the preparation of new naphthyridones (16) and (17).