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■ Mono and Sequential Bis Solid Phase Alkylations of a (R)-Phenylglycinol Derived Pyrrolidinone Scaffold

Armand Blommaert, Philippe James, Fanny Valleix, Henri-Philippe Husson, and Jacques Royer*

*Laboratoire de Chimie Thérapeutique associé au C.N.R.S., Faculté des Sciences Pharmaceutiques et Biologiques, Université René Descartes, 4, avenue de l'Observatoire 75270 Pairs Cedex 06, France

Abstract

The preparation of piperidine- and pyrrolidinone-like polymer supported (R)-phenylglycinol derived scaffolds is described. Alkylation reactions were performed as a model transformation of these templates on the solid support which highlight some specific limitations in the use of (R)-phenylglycinol on the resin. Whereas the polymer supported piperidine was completely void of reactivity, alkylation of the pyrrolidinone counterpart proceeded with good yield, purity and control of mono- over bis-alkylation but with low diastereomeric excess.