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

S. Mascarella; Ken S. Rehder; Desong Zhong; Anne M. Miller; Scott P. Runyon; Timothy R. Fennell; David Hesk; Anne M. Miller; David Hesk; D M Lindsay; W J Kerr; Ken S. Rehder; Timothy R. Fennell; S. Wayne Mascarella; Desong Zhong; Scott P. Runyon

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

Queen, A. E., Hesk, D., Lindsay, D. M., Kerr, W. J., Rehder, K., Fennell, T., Mascarella, W., Zhong, D., & Runyon, S. (2020). Synthesis of [H-3] and [C-14]genipin. Journal of Labelled Compounds and Radiopharmaceuticals, 63(4), 196-202. https://doi.org/10.1002/jlcr.3832

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Abstract

[H-3]Genipin was synthesized in a single step by Ir(I) catalyzed hydrogen isotope exchange. Conditions for selective exchange of the sp(2) 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 [H-3]genipin at a specific activity of 18.5 Ci/mmol. Racemic [C-14]genipin was prepared in eight steps in overall 5.4% radiochemical yield from potassium [C-14]cyanide.