An efficient two-step synthesis of 3-amino-1-benzhydrylazetidine

ORGN 553

Michael Witt1, Bryan Li, bryan.li@pfizer.com2, Thomas A. Brandt2, and David Whritenour2. (1) Pfizer Global Research and Development, Eastern Point Road, Groton, CT 06340, (2) Chemical Research and Development, Pfizer Global Research and Development, Eastern Point Road, Groton, CT 06340
A streamlined process for the synthesis of 3-amino-1-benzhydrylazetidine is described. Commercially available 1-benzhydrylazetidin-3-ol was reacted with methanesulfonyl chloride in the presence of triethylamine in acetonitrile, upon quench with water, the mesylate intermediate (3) was isolated by filtration. The wet filter cake was subsequently treated with ammonium hydroxide/isopropanol in a Parr reactor at ~70°C. The procedure afforded the titled compound as mono acetate salt in 72 – 84% yield.