Titania-catalyzed radiofluorination of tosylated precursors in highly aqueous medium

Sergeev, Maxim E.; Morgia, Federica; Lazari, Mark; Wang, Jr., Christopher; van Dam, R. Michael

doi:10.1021/jacs.5b02659

Titania-catalyzed radiofluorination of tosylated precursors in highly aqueous medium

Journal Article · Fri Apr 10 04:00:00 EDT 2015 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.5b02659· OSTI ID:1345980

Sergeev, Maxim E. ^[1]; Morgia, Federica ^[2]; Lazari, Mark ^[2]; Wang, Jr., Christopher ^[2]; van Dam, R. Michael ^[2]

David Geffen School of Medicine at Univ. of California, Los Angeles, CA (United States); Office of Scientific and Technical Information (OSTI)
David Geffen School of Medicine at Univ. of California, Los Angeles, CA (United States)

Nucleophilic radiofluorination is an efficient synthetic route to many positron-emission tomography (PET) probes, but removal of water to activate the cyclotron-produced [¹⁸F]fluoride has to be performed prior to reaction, which significantly increases overall radiolabeling time and causes radioactivity loss. In this paper, we demonstrate the possibility of ¹⁸F-radiofluorination in highly aqueous medium. The method utilizes titania nanoparticles, 1:1 (v/v) acetonitrile–thexyl alcohol solvent mixture, and tetra-n-butylammonium bicarbonate as a phase-transfer agent. Efficient radiolabeling is directly performed with aqueous [¹⁸F]fluoride without the need for a drying/azeotroping step to significantly reduce radiosynthesis time. High radiochemical purity of the target compound is also achieved. Finally, the substrate scope of the synthetic strategy is demonstrated with a range of aromatic, aliphatic, and cycloaliphatic tosylated precursors.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of California, Los Angeles, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)

Grant/Contract Number:: SC0001249

OSTI ID:: 1345980

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 17 Vol. 137; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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