Synthesis of Halogenomethylaminoalcohols and Halogenomethylaminodiols

The reduction of trihalogenomethylnitroalcohols (1) and trihalogenomethylnitrodiols (2) as the compounds containing trihalogenomethyl radical of potential therapeutic interest were examined by different methods.It was confirmed that (1) had been reduced to trihalogenometylhydroxylaminoalcohols (3) by catalytic hydrogenation but one of the chlorine atoms in (1) had been removed by hydrogenolysis and had been reduced to dihalogenomethylaminoalcohols (4) and (3) by electrolytic reduction. Trihalogenomethylaminoalcohols (5) and trihalogenomethylaminodiols (6) were synthesized by the reduction of (1) and (2) with tin and hydrochloric acid.