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Base/cryptand/metal-free automated nucleophilic radiofluorination of [ 18 F]FDOPA from iodonium salts: importance of hydrogen carbonate counter ion

Abstract : As evidenced by the number of publications and patents published in the last years, the radiosynthesis of 6-[ 18 F]fluoro-3,4-dihydroxy-L-phenylalanine ([ 18 F]FDOPA) using nucleophilic [ 18 F]F-process remains currently a challenge for the radiochemists scientific community even if promising methods for the radiofluorination of electron-rich aromatic structures were recently developed from arylboronate, arylstannane or iodoniums salts precursors. In such context, based on the use of an iodonium triflate salt precursor, we optimized a fast and efficient radiofluorination route fully automated and free from any base, cryptand or metal catalyst for the radiosynthesis of [ 18 F]FDOPA. Using this method, this clinically relevant radiotracer was produced in 64 min, 27-38% RCY d.c. (n = 5), >99% RCP, >99% e.e., and high molar activity 170-230 GBq/µmol. In addition, this optimisation study clearly highlighted the important role of a triflate-hydrogen carbonate counterion exchange during the radiolabelling process to achieve high fluorine-18 incorporation yields.
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Submitted on : Saturday, November 2, 2019 - 1:44:48 PM
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Aurélie Maisonial-Besset, Audrey Serre, Ali Ouadi, Sébastien Schmitt, Damien Canitrot, et al.. Base/cryptand/metal-free automated nucleophilic radiofluorination of [ 18 F]FDOPA from iodonium salts: importance of hydrogen carbonate counter ion. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2018, 2018 (48), pp.7058-7065. ⟨10.1002/ejoc.201801608⟩. ⟨hal-02343361⟩

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