A practical synthesis of para di- and mono-substituted benzhydrylamines from benzhydrol precursors

A series of para-substituted benzhydrylamines 6 were obtained by substituti on of the corresponding benzhydrol precursors 1 with phenyl carbamate 2 und er acidic conditions, followed by basic hydrolysis of the carbamate interme diates 3. One unsymmetrical intermediate 3i has been resolved by preparativ e chiral chromatography. Subsequent deprotection of the carbamate function led to the recovery of enantiomerically pure (+)- and (-)-4-chlorobenzhydry l amines.