Synthesis of chiral 2-amino-1-phenylethanol

Two methods for the synthesis of chiral 2-amino-1-phenyl ethanol have been developed. The first utilizes a chiral oxaborolidine catalyzed borane reduction of phenacyl chloride to give the chiral chloro-alcohol in very good yield with an ee in the 93%-97% range. Reaction with dilute ammonium hydroxide produced the amino-alcohol in very good yield with a high ee. The second approach involved first conversion of the phenacyl chloride to the succinimide which was then hydrogenated using a chiral ruthenium complex in conjuction with a base and an optically active amine (Noyori procedure) to give the optically active succinimido alcohol in very good yield with an ee of 98%. Hydrolysis with dilute base produced the optically active amino alcohol in very good yield and excellent enantioselectivity.