Patent ID: 6448449
Filing Date: 2002-09-10
Classification: C07B,C07C,C07F

Abstract:
A process for the preparation of an (R)-1-(aryloxy)propan-2-ol with high regioselectivity and enantioselectivity, said process comprising the steps of:contacting an aryl trialkysilyl ether and (R)-propylene oxide in the presence of a catalyst to produce a regioisomeric mixture of (R)-1-(aryloxy)-2-trialkylsiloxypropane and (S)-2-(aryloxy)-1-trialkylsiloxypropane; contacting said regioisomeric mixture of said (R)-1-aryloxy-2-trialkylsiloxypropane and said (S)-2-(aryloxy)-1-trialkylsiloxypropane and an alcohol in the presence of an acid at a temperature and for a length of time sufficient to produce a regioisomeric mixture of (R)-1-(aryloxy)propan-2-ol and (S)-2-(aryloxy)propane-1-ol; contacting said regioisomeric mixture of (R)-1-(aryloxy)propan-2-ol and (S)-2-(aryloxy)propane-1-ol and a triarylmethyl halide in the presence of a base at a temperature and for a length of time sufficient to produce a crude mixture of (R)-1-(aryloxy)propan-2-ol and (S)-2-(aryloxy)-1-triarylmethyloxypropane; and distilling said crude mixture of (R)-1-(aryloxy)propan-2-ol and (S)-2-(aryloxy)-1-triarylmethyloxypropane to isolate said (R)-1-(aryloxy)propan-2-ol from said crude mixture.