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Synthesis of fluorine-18 labeled GABA uptake inhibitors

✍ Scribed by Michael R. Kilbourn; Michael R. Pavia; Vlad E. Gregor

Book ID
103922359
Publisher
Elsevier Science
Year
1990
Weight
623 KB
Volume
41
Category
Article
ISSN
0883-2889

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✦ Synopsis

The first syntheses of fluorine-18 labeled inhibitors of GABA reuptake [(R,S)-I-{2-{4-['*F]fluoropheny1}pheny1}methoxyethyl]piperidine-3-carboxy1ic acid, (R,S)-I-{2-(4-["F]fluorophenyl)(4fluorophenyl)methoxyethyl}piperidine-3-carboxylic acid, and (R,S)-I-[2-((4~['*F]trifluoromethyl)phenyl} { (4-trifluoromethyl)phenyl)-methoxyethyl]pi~ridine-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 ["Flbenzhydryl chlorides (prepared in three steps from ['*F]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 ['sF]trifluoromethyl group by the nucleophilic substitution of a bromodifluoromethyl substituent has also been developed.

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