Large-scale synthesis of (S)-2-hydroxyamino-2-phenylethanol

ORGN 168

Timothy B. Towne,, Wenke Li,, Gregory S. Wayne, Steven J. Wittenberger, and Steve Richter, GPRD Process Chemistry, Abbott Laboratories, 1401 Sheridan Road, North Chicago, IL 60064
Optically pure 2-hydroxyamino-2-phenylethanol is an important chiral auxiliary often used in 1,3-dipolar cycloaddition of nitrones to form chiral isoxazolidines. In support of an ongoing drug development project, a robust process was developed and successfully demonstrated on a 44 Kg scale. Process optimization and hazard analysis will be presented.