Synthesis and separation of stereoisomers of 1,4- and 2,4-dihydroxyadamantanes

Abstract

Mixture of isomers of 1,4-dihydroxyadamantane has been prepared by reduction of 5-hydroxyadamantane-2-one, the isomeric 2,4-dihydroxyadamantanes have been prepared by reduction of adamantane-2,4-dione. The mixtures of 1,4- and 2,4-dihydroxyadamantanes have been separated into pure stereoisomers by elution chromatography on a silica gel column using benzene and diethyl ether as eluents. Structures of the individual isomers have been confirmed by NMR spectroscopy.