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Synthesis of [ 3 H] and [ 14 C]genipin
Author(s) -
Queen Adele.E.,
Hesk David,
Lindsay David.M.,
Kerr William.J.,
Rehder Kenneth,
Fennell Tim,
Mascarella Wayne,
Zhong Desong,
Runyon Scott
Publication year - 2020
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3832
Subject(s) - genipin , yield (engineering) , tritium , chemistry , catalysis , deuterium , radiochemistry , nuclear chemistry , hydrogen , hydrogen cyanide , organic chemistry , medicinal chemistry , materials science , physics , quantum mechanics , chitosan , nuclear physics , metallurgy
[ 3 H]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 [ 3 H]genipin at a specific activity of 18.5 Ci/mmol. Racemic [ 14 C]genipin was prepared in eight steps in overall 5.4% radiochemical yield from potassium [ 14 C]cyanide.
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