One-pot synthesis of high molar activity 6-[18F]fluoro-l-DOPA by Cu-mediated fluorination of a BPin precursor

Andrew V Mossine; Sean S Tanzey; Allen F Brooks; Katarina J Makaravage; Naoko Ichiishi; Jason M Miller; Bradford D Henderson; Marc B Skaddan; Melanie S Sanford; Peter J H Scott

doi:10.1039/c9ob01758e

One-pot synthesis of high molar activity 6-[¹⁸F]fluoro-l-DOPA by Cu-mediated fluorination of a BPin precursor

Org Biomol Chem. 2019 Oct 14;17(38):8701-8705. doi: 10.1039/c9ob01758e. Epub 2019 Sep 19.

Affiliations

¹ Department of Radiology, University of Michigan, Ann Arbor, MI 48109, USA. pjhscott@umich.edu.
² Department of Radiology, University of Michigan, Ann Arbor, MI 48109, USA. pjhscott@umich.edu and Department of Medicinal Chemistry, University of Michigan, Ann Arbor, MI 48109, USA.
³ Department of Chemistry, University of Michigan, Ann Arbor, MI 48109, USA. mssanfor@umich.edu.
⁴ AbbVie Translational Imaging, North Chicago, IL 60030, USA.

Abstract

A one-pot two-step synthesis of 6-[¹⁸F]fluoro-l-DOPA ([¹⁸F]FDOPA) has been developed involving Cu-mediated radiofluorination of a pinacol boronate ester precursor. The method is fully automated, provides [¹⁸F]FDOPA in good activity yield (104 ± 16 mCi, 6 ± 1%), excellent radiochemical purity (>99%) and high molar activity (3799 ± 2087 Ci mmol^-1), n = 3, and has been validated to produce the radiotracer for human use.

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Copper / chemistry*
Halogenation
Humans
Molecular Structure
Radiopharmaceuticals / chemical synthesis*
Radiopharmaceuticals / chemistry

Substances

Radiopharmaceuticals
Copper

Grants and funding

R01 EB021155/EB/NIBIB NIH HHS/United States