A method for the synthesis of 2‐amino‐4‐fluoro‐bicyclo[3.1.0]hexane‐2,6‐dicarboxylic acid‐[3H2]

A process for double deuterium labeling of an alcohol was developed. The process was utilized in the subsequent tritium labeling of a secondary alcohol with high specific activity (24 Ci/mmol) by reduction of the corresponding ketone using sodium borotritide. The starting ketone was first brominated with pyridinium tribromide; the resulting alpha bromoketone was then reduced in THF/alcohol in the presence of Ni(OAc)₂. The alcohol was then converted to 2‐amino‐4‐fluorobicyclo[3.1.0]hexane‐2,6‐dicarboxylic acid‐[³H₂], an mGluR agonist. Copyright © 2004 John Wiley & Sons, Ltd.