Stereoselective synthesis of (2 S,3 S)-3-hydroxy-2-phenylpiperidines, precursors of non-peptidic substance P antagonists

Abstract

(2 S)- N-Boc-3-oxo-2-phenylpiperidine 5 and (2 S,3 S)- N-Boc-3-hydroxy-2-phenylpiperidine 6, known chiral building blocks for the synthesis of non-peptidic substance P antagonists, were prepared from erythro (2 S)- N-benzyl 2-hydroxybenzylpyrrolidine derived from ( S)- N-methoxy- N-methylpyroglutamide.