Synthesis of [3H] and [14C]genipin. (11th February 2020)

• Record Type: Journal Article
• Authors: Queen, Adele.E.; Hesk, David; Lindsay, David.M.; Kerr, William.J.; Rehder, Kenneth; Fennell, Tim; Mascarella, Wayne; Zhong, Desong; Runyon, Scott
• Is Part Of: Journal of labelled compounds & radiopharmaceuticals. Volume 63:Number 4(2020)
• Page Start: 196
• Page End: 202
• Publication Date: 2020-02-11
• Subjects: carbon‐14 -- Gardenia Blue -- genipin -- Iridium (I) -- Otera's catalyst -- tritium; Tracers (Chemistry) -- Periodicals; Radiopharmaceuticals -- Periodicals; 615.8424
• DOI: 10.1002/jlcr.3832
• Languages: English
• ISSNs: 0362-4803

Abstract

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.