Synthesis of [3H] and [14C]genipin. (11th February 2020) - Queen, Adele.E.
Abstract : [ 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. Abstract : [ 3 H]genipin was prepared by Ir(I) catalysed hydrogen isotope exchange. [ 14 C]genipin was prepared in 8 steps from K[14]CN.