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Synthesis of fluorine-18 labeled GABA uptake inhibitors.

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  • 1. Division of Nuclear Medicine, University of Michigan, Ann Arbor.
      Authors
    • Kilbourn MR 1
    (1 author)

International Journal of Radiation Applications and instrumentation. Part A, Applied Radiation and Isotopes, 01 Jan 1990, 41(9):823-828
https://doi.org/10.1016/0883-2889(90)90059-p PMID: 2176190 

Abstract 

The first syntheses of fluorine-18 labeled inhibitors of GABA reuptake [(R,S)-1-[2-[4-[18F]fluorophenyl]phenyl]methoxyethyl]piperidine- 3-carboxylic acid, (R,S)-1-[2-[(4-[18F]trifluoromethyl)phenyl][(4- trifluoromethyl)phenyl]-methoxyethyl]piperidine-3-carboxylic acid] are described. These N-substituted nipecotic acid derivatives were prepared in no-carrier-added form by the condensation of the appropriately substituted [18F]benzhydryl chlorides (prepared in three steps from [18F]fluoride ion) with N-(2-hydroxyethyl)nipecotic acid ethyl ester, followed by ester hydrolysis. Overall radiochemical yields were 17-28% (corrected, 150 min synthesis time). A simple new method for synthesis of a [18F]trifluoromethyl group by the nucleophilic substitution of a bromodifluoromethyl substituent has also been developed.

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Funding 

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NINDS NIH HHS (1)