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A method for the synthesis of 2‐amino‐4‐fluoro‐bicyclo[3.1.0]hexane‐2,6‐dicarboxylic acid‐[ 3 H 2 ]
Author(s) -
Kuo Fengjiun,
Kulanthaivel Palaniappan,
Rener Gregory A.,
Yi Ping,
Wheeler William J.
Publication year - 2004
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.843
Subject(s) - chemistry , alcohol , ketone , hexane , dicarboxylic acid , bicyclic molecule , organic chemistry , pyridinium , medicinal chemistry
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‐[ 3 H 2 ], an mGluR agonist. Copyright © 2004 John Wiley & Sons, Ltd.