Synthesis of (3-Hydroxyadamantan-1-yl)methanols

A convenient procedure has been developed for the synthesis of (3-hydroxyadamantan-1-yl)-methanols on the basis of nitroxylation of adamantan-1-ylmethanols with fuming nitring acid and subsequent reduction of intermediate nitric acid esters with hydrazine hydrate. The title diols have also been obtained by the reduction of 1-nitroxy-3-(nitroxymethyl)adamantanes. The nitroxylation process is accompanied by oxidation with the formation of substituted adamantane-1-carboxylic acids.