Synthesis of [3H] and [14C]genipin

Adele E. Queen, David Hesk, David M. Lindsay, William J. Kerr, Kenneth Rehder, Tim Fennell, Wayne Mascarella, Desong Zhong, Scott Runyon

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Abstract

[3H]Genipin was synthesized in a single step by Ir(I) catalyzed hydrogen isotope exchange. Conditions for selective exchange of the sp2 CH bond ortho to the methyl ester functionality were developed through deuterium modeling studies through a catalyst screen. Optimized conditions so obtained were then utilized with tritium gas to generate [3H]genipin at a specific activity of 18.5 Ci/mmol. Racemic [14C]genipin was prepared in eight steps in overall 5.4% radiochemical yield from potassium [14C]cyanide.
Original languageEnglish
Pages (from-to)196-202
Number of pages7
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume63
Issue number4
Early online date4 Feb 2020
DOIs
Publication statusPublished - 30 Apr 2020

Keywords

  • carbon-14
  • gardenia blue
  • genipin
  • Iridium (I)
  • Otera's catalyst
  • tritium

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