Simple and efficient synthesis of 2-[(18)F]fluoroethyl triflate for high yield (18)fluoroethylation

Appl Radiat Isot. 2014 Dec:94:141-146. doi: 10.1016/j.apradiso.2014.07.016. Epub 2014 Aug 4.

Abstract

The [(18)F]fluoroethyl moiety has been widely utilized in the synthesis of (18)F-labelled compounds. The aim of this work was the reliable synthesis of [(18)F]FEtOTf with a novel strategy to increase the reactivity of the commonly used [(18)F]FEB and [(18)F]FEtOTos. [(18)F]FEtOTf and the intermediate [(18)F]FEtOH were synthesized in high RCY (78% and 85%, respectively) and purified by SPE. The high potency of [(18)F]FEtOTf was shown by the efficient alkylation of the deactivated nucleophile aniline under mild conditions, as well as by the synthesis of [(18)F]FEC.

Keywords: (18)F-fluoroethylation; 2-[(18)F]fluoroethanol; 2-[(18)F]fluoroethyl triflate; Fluorine-18.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fluorine Radioisotopes / chemistry*
  • Fluorine Radioisotopes / isolation & purification*
  • Isotope Labeling / methods*
  • Mesylates / chemical synthesis*
  • Mesylates / isolation & purification*
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / isolation & purification*
  • Vinyl Compounds / chemistry

Substances

  • Fluorine Radioisotopes
  • Mesylates
  • Radiopharmaceuticals
  • Vinyl Compounds
  • vinyl fluoride