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A series of 1-benzyl-3-hydroxy-1,2,3,6-tetrahydropyridines, multipurpose synthons for fine organic synthesis and potential antiviral compounds, was prepared by the rearrangement of a number of 1-benzyl-3,4epoxypiperidines under treatment with lithium amides. 3,4-Epoxypiperidines were obtained by oxidation of 1,2,5,6tetrahydropyridines trifluoroacetates with a trifluoroperacetic acid. Convenient synthetic routes were found and developed. A conformation analysis of the series of stable 3,4-epoxypiperidines and 3-hydroxy-1,2,3,6tetrahydropyridines was carried out.

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Enantiomerically pure trans-(3R,4R)-4-aminopiperidin-3-ols, which are convenient precursors for making natural and synthetic aminohydroxylated piperidine alkaloid analogs, were efficiently synthesized through the reaction of enantiomerically pure (3R,4S)-3,4-epoxypiperidine with amines in the presence of LiClO 4 in CH 3 CN at room temperature. The absolute stereochemistry of the resultant amino alcohols was determined by the stereochemical correlation method and single-crystal X-ray analysis.