Syntheses with stable isotopes: synthesis of deuterium and 13C labeled bile acids

Article abstract of DOI:10.1002/jlcr.2590090412

A series of 5β cholanic acids labeled with deuterium in the A ring were prepared by exchange labeling of the corresponding ketone by column chromatography on deuterated alumina. Factors affecting yield and labeling efficiency are discussed. 5β Cholanic acids labeled with ¹³C in the carboxyl position were prepared by treatment of the corresponding 23 chloro 24 norcholane with sodium cyanide ¹³C followed by alkaline hydrolysis of the nitrile. The intermediates in the synthesis were characterized by high resolution NMR spectroscopy. Mass spectra are also reported for the ¹³C labeled products.