Efficient Synthesis of a New Series of Piperidine Ring–Modified Alcohol and Methyl Ether Analogs of (±)-threo-Methyl Phenyl(piperidin-2-yl)acetate

Abstract

A series of novel piperidine ring–modified alcohol and methyl ether analogs of (±)-threo-methyl phenyl(piperidin-2-yl)acetate was synthesized. This series of methyl phenyl(piperidin-2-yl)acetate analogs was developed by piperidine ring alkylation and/or acylation followed by lithium aluminum hydride reduction to give alcohol derivatives. Methylation of the alcohol analogs by extension of standard literature procedures gave the corresponding methyl ether derivatives. The chemical structure of these compounds was established based on mass and 1H NMR spectral data and CHN elemental analysis data. Several significant modifications to the literature methodologies made the reaction more efficient, and good yields were generally obtained.