Electrochemical nucleophilic synthesis of di-tert-butyl-(4-[F-18]fluoro-1,2-phenylene)-dicarbonate
2014 (English)In: Applied Radiation and Isotopes, ISSN 0969-8043, E-ISSN 1872-9800, Vol. 92, 52-57 p.Article in journal (Refereed) Published
An electrochemical method with the ability to conduct F-18-fluorination of aromatic molecules through direct nucleophilic fluorination of cationic intermediates is presented in this paper. The reaction was performed on a remote-controlled automatic platform. Nucleophilic electrochemical fluorination of tert-butyloxycarbonyl (Boc) protected catechol, an intermediate model molecule for the positron emission tomography (PET) probe (3,4-dihydroxy-6-[F-18]fluoro-L-phenylalanine), was performed. Fluorination was achieved under potentiostatic anodic oxidation in acetonitrile containing Et3N center dot 3HF and other supporting electrolytes. Radiofluorination efficiency was influenced by a number of variables, including the concentration of the precursor, concentration of Et3N center dot 3HF, type of supporting electrolyte, temperature and time, as well as applied potentials. Radiofluorination efficiency of 10.4 +/- 0.6% (n=4) and specific activity of up to 43 GBq/mmol was obtained after 1 h electrolysis of 0.1 M of 4-tert-butyl-diboc-catechol in the acetonitrile solution of Et3N center dot 3HF (0.033 M) and NBu4PF6 (0.05 M). Density functional theory (DFT) was employed to explain the tert-butyl functional group facilitation of electrochemical oxidation and subsequent fluorination.
Place, publisher, year, edition, pages
2014. Vol. 92, 52-57 p.
PET, Radiochemistry, Electrochemical radiosynthesis, Nucleophilic radiofluorination, Aromatic substitution, DFT simulation
Radiology, Nuclear Medicine and Medical Imaging
IdentifiersURN: urn:nbn:se:kth:diva-153262DOI: 10.1016/j.apradiso.2014.06.013ISI: 000341476700010ScopusID: 2-s2.0-84903847327OAI: oai:DiVA.org:kth-153262DiVA: diva2:753863
QC 201410092014-10-092014-10-032014-10-09Bibliographically approved