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Aryltrimethylammonium trifluoromethanesulfonates as precursors to aryl [ 18 F]fluorides: Improved synthesis of [ 18 F]GBR‐13119
Author(s) -
Haka Michael S.,
Kilbourn Michael R.,
Leonard Watkins G.,
Toorongian Steven A.
Publication year - 1989
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.2580270711
Subject(s) - chemistry , yield (engineering) , trifluoromethanesulfonate , piperazine , fluoride , radiochemistry , medicinal chemistry , nucleophilic substitution , nuclear chemistry , aryl , high performance liquid chromatography , organic chemistry , inorganic chemistry , catalysis , materials science , alkyl , metallurgy
Aromatic nucleophilic substitution of various trimethylammonium trifluoromethanesulfonates with [ 18 F]fluoride has been evaluated. Fluorinations were studied over a temperature range of 45–165°C, with decay corrected yields ranging from 20–80%. [ 18 F]GBR 13119, 1‐[2‐{(4‐[ 18 F]fluorophenyl)(phenyl)methoxy}ethyl]‐4‐(3‐phenylpropyl)piperazine, a potential radio‐tracer for the dopamine uptake system, has been prepared in no‐carrier‐added form from 4‐N,N,N,‐trimethylaniliniumphenylmethanone trifluoromethanesulfonate. Purification by solid‐phase techniques yielded the product in 20% decay corrected radiochemical yield and >98% radiochemical and chemical purity without HPLC.