[18F]Fluoromethyl triflate, a novel and reactive [18F]fluoromethylating agent: Preparation and application to the on-column preparation of [18F]fluorocholine

Ren Iwata, Claudio Pascali, Anna Bogni, Shozo Furumoto, Kazunori Terasaki, Kazuhiko Yanai

Research output: Contribution to journalArticle

68 Citations (Scopus)

Abstract

The production and use of [18F]fluoromethyl triflate ([18F]CH2FOTf), a more reactive [18F]fluoromethylating agent than [18F]fluoromethyl bromide ([18F]CH2BrF), is described. [18F]CH2FOTf was prepared from [18F]CH2BrF. The latter was synthesized by nucleophilic substitution of CH2Br2 with no-carrier-added [18F]fluoride and purified by four Sep-Pak Plus silica cartridges connected in series. It was then quantitatively converted on-line to [18F]CH2FOTf by passing through a heated AgOTf column. Decay-corrected radiochemical yields of [18F]CH2FOTf based on [18F]fluoride were 47±8% (n=20). Both [18F]CH2BrF and [18F]CH2FOTf were applied to solid-supported [18F]fluoromethylation of N,N-dimethylaminoethanol on a Sep-Pak Plus C18 cartridge to produce the 18F-labeled choline analogue, (β-hydroxyethyl)dimethyl-[18F]fluoromethylammonium ([18F]fluorocholine). Depending on flow rate and amount of precursor used, decay corrected radiochemical yields of [18F]fluorocholine from [18F]CH2BrF ranged from 6% to 63%, while [18F]CH2FOTf afforded yields of more than 80%. Thus, by using the latter reagent and a subsequent purification on a Sep-Pak Accell CM cartridge, [18F]fluorocholine was produced from [18F]fluoride in overall radiochemical yields of 40% (decay corrected) in less than 30 min.

Original languageEnglish
Pages (from-to)347-352
Number of pages6
JournalApplied Radiation and Isotopes
Volume57
Issue number3
DOIs
Publication statusPublished - 2002 Jul 23

Keywords

  • F-18
  • Fluorocholine
  • Fluoromethyl bromide
  • Fluoromethyl triflate
  • Radiosynthesis

ASJC Scopus subject areas

  • Radiation

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