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. 2017 Sep:127:245-252.
doi: 10.1016/j.apradiso.2017.06.028. Epub 2017 Jun 21.

An automated synthesizer for electrochemical 18F-fluorination of organic compounds

Affiliations

An automated synthesizer for electrochemical 18F-fluorination of organic compounds

Christopher M Waldmann et al. Appl Radiat Isot. 2017 Sep.

Abstract

Electrochemical 18F-fluorination of organic compounds provides a means to synthesize Positron-Emission-Tomography (PET) tracers difficult to obtain otherwise. Here, the first automated synthesizer that enables radiolabeling through carrier-added electrochemical 18F-fluorination is described. The system provides capabilities for all necessary operations such as drying of cyclotron derived [18F]fluoride, electrochemical incorporation of the radioisotope into a precursor molecule, subsequent reactions such as protecting group removals, HPLC-purification and formulation of the final tracer. Demonstrated is the aliphatic electrochemical 18F-fluorination of methyl 2-(phenylthio)acetate.

Keywords: Electrochemistry; Late-stage fluorination; PET; Radiosynthesizer; [(18)F]fluoride.

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Figures

Fig. 1
Fig. 1
Electrochemical 18F-fluorination described by He et al.
Fig. 2
Fig. 2
Carrier-added 18F-fluorination of methyl 2-(phenylthio)acetate (3).
Fig. 3
Fig. 3
The graphical user interface (GUI) of the control software showing the schematic of the platform.
Fig. 4
Fig. 4
Schematic of the electrochemical cell.
Fig. 5
Fig. 5
Sample CVs of ‘blank’ (blue) and ‘substrate’ (orange) solutions.
Fig. 6
Fig. 6
Effect of the Et4NF · 4HF concentration on RCY and Am.
Fig. 7
Fig. 7
Decay corrected (d.c.) and non-decay corrected (n.d.c.) RCY with increasing electrolysis times.

References

    1. Cole EL, Stewart MN, Littich R, Hoareau R, Scott PJH. Radiosyntheses using Fluorine-18: the art and science of late stage fluorination. Curr Top Med Chem. 2014;14:875–900. - PMC - PubMed
    1. Fuchigami T, Konno A, Nakagawa K, Shimojo M. Electrolytic partial fluorination of organic compounds. 12. Selective anodic monofluorination of fluoroalkyl and alkyl sulfides. J Org Chem. 1994;59:5937–5941.
    1. Fuchigami T, Inagi S. Selective electrochemical fluorination of organic molecules and macromolecules in ionic liquids. Chem Commun. 2011;47:10211–10223. - PubMed
    1. Fuchigami T, Kayoko Y, Akinori K. Electrolytic reactions of fluoro organic compounds. 8. Further study on anodic methoxylation and acetoxylation of aryl fluoroalkyl sulfides. Tetrahedron. 1991;47:625–634.
    1. Gao Z, et al. Metal-free oxidative fluorination of phenols with [18F]fluoride. Angew Chem Int Ed. 2012;51:6733–6737. - PubMed

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