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Syntheses with stable isotopes: Synthesis of deuterium and 13 C labeled bile acids
Author(s) -
Hachey D. L.,
Szczepanik P. A.,
Berngruber O. W.,
Klein P. D.
Publication year - 1973
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590090412
Subject(s) - chemistry , nitrile , deuterium , hydrolysis , yield (engineering) , alkaline hydrolysis , nuclear magnetic resonance spectroscopy , mass spectrometry , organic chemistry , radiochemistry , chromatography , physics , materials science , quantum mechanics , metallurgy
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 13 C in the carboxyl position were prepared by treatment of the corresponding 23‐chloro‐24‐norcholane with sodium cyanide‐ 13 C 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 13 C labeled products.