Synthesis of diastereoisomeric 4-dimethylamino-3-phenyl-2-butanols and related esters for antimicrobial evaluation

4-Dimethylamino-3-phenyl-2-butanone was reduced to the corresponding diastereoisomeric alcohols, which were separated by fractional crystallization of the corresponding hydrochloride salts. The configuration of the diastereoisomeric alcohols was determined by PMR spectroscopy. The assignments were confirmed by a consideration of the mass spectral data obtained for the two alcohols. Acylation of the alcohols gave the corresponding esters. Antimicrobial evaluation of the compounds prepared showed that 4-dimethylamino-3-phenyl-2-butanone had a promising level of antifungal activity while the other derivatives showed either a low level of potency or were inactive.