ChemInform Abstract: 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.

Abstract

Preparationof (1R,4R)-1-Methyl-2-(p-toluenesulfonyl)-5phenylmethyl-2, 5-diazabicyclo-(2.2.1)heptane, Intermediate in a Synthesis of New Naphthyridones.-Starting with trans-4-hydroxy-L-proline (I), the chiral diazabicycloheptane (XVI) mentioned in the title is synthesized as outlined in the reaction scheme. The compound (XVI) is detosylated and then coupled with 7-chloronaphthyridines, e.g. (XVIII), to give the adduct (XIX). Final deprotection yields the naphthyridone (XX) which shows antibacterial activity in vitro. -(REMUZON, P.; MASSOUDI, M.; BOUZARD, D.; JACQUET, J.-P.; Heterocycles 34 (1992) 4, 679-684; Bristol-Myers Squibb Pharm. Res. Inst., 77422 Marne-la-Vallee, Fr.; EN)