Article (Scientific journals)
Highly enantioselective synthesis of no-carrier-added 6-[18F]Fluoro-L-dopa by chiral phase-transfer alkylation
Lemaire, Christian; Gillet, Steve; Guillouet, Stéphane et al.
2004In European Journal of Organic Chemistry, (13), p. 2899-2904
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Keywords :
Amino acids; Enantioselectivity; Fluorides; Radiochemistry; Radiopharmaceuticals; Phase-transfer catalysis
Abstract :
[en] [F-18]Fluoro-L-dopa, an important radiopharmaceutical for positron emission tomography (PET), has been synthesized using a phase-transfer alkylation reaction. A chiral quaternary ammonium salt derived from a Cinchona alkaloid served as phase-transfer catalyst for the enantioselective alkylation of a glycine derivative. The active methylene group of this Schiff-base substrate was deprotonated with cesium hydroxide and rapidly alkylated by the 2-[F-18]fluoro-4,5-dimethoxybenzyl halide (X = Br, I). The reaction proceeded with high yield (> 90%) at 0 degreesC or room temperature in various solvents such as toluene or dichloromethane. Preparation of the [F-18]alkylating agent on a solid support was developed. After labelling, the labeled [F-18]fluoroveratraldehyde was trapped on a (t)C18 cartridge and then converted on the cartridge into the corresponding benzyl halide derivatives by addition of aqueous sodium borohydride and gaseous hydrobromic or -iodic acid. Hydrolysis and purification by preparative HPLC made 6-[F-18]fluoro-L-dopa ready for human injection in a 25-30% decay-corrected radiochemical yield in a synthesis time of 100 min. The product was found to be chemically, radiochemically and enantiomerically pure (ee > 95%). (C) Wiley-VCH Verlag GmbH
Research center :
GIGA CRC (Cyclotron Research Center) In vivo Imaging-Aging & Memory - ULiège
CERMEP Lyon
Disciplines :
Chemistry
Author, co-author :
Lemaire, Christian ;  Université de Liège - ULiège > Centre de recherches du cyclotron
Gillet, Steve
Guillouet, Stéphane
Plenevaux, Alain  ;  Université de Liège - ULiège > Centre de recherches du cyclotron
Aerts, Joël ;  Université de Liège - ULiège > Centre de recherches du cyclotron
Luxen, André ;  Université de Liège - ULiège > Département de chimie (sciences) > Chimie organique de synthèse - Centre de recherches du cyclotron
Language :
English
Title :
Highly enantioselective synthesis of no-carrier-added 6-[18F]Fluoro-L-dopa by chiral phase-transfer alkylation
Publication date :
28 June 2004
Journal title :
European Journal of Organic Chemistry
ISSN :
1434-193X
eISSN :
1099-0690
Publisher :
Wiley VCH Verlag, Weinheim, Germany
Issue :
13
Pages :
2899-2904
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE]
Available on ORBi :
since 29 January 2009

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