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

Queen, Adele E. and Hesk, David and Lindsay, David M. and Kerr, William J. and Rehder, Kenneth and Fennell, Tim and Mascarella, Wayne and Zhong, Desong and Runyon, Scott (2020) Synthesis of [3H] and [14C]genipin. Journal of Labelled Compounds and Radiopharmaceuticals, 63 (4). pp. 196-202. ISSN 0362-4803

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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.