1. Synthesis of [3H] and [14C]genipin.
- Author
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Queen, Adele.E., Hesk, David, Lindsay, David.M., Kerr, William.J., Rehder, Kenneth, Fennell, Tim, Mascarella, Wayne, Zhong, Desong, and Runyon, Scott
- Subjects
HYDROGEN isotopes ,DEUTERIUM ,TRITIUM ,ISOTOPE exchange reactions ,METHYL formate ,CYANIDES - 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. [ABSTRACT FROM AUTHOR]
- Published
- 2020
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