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Tritium labeled trans‐4‐n‐butyl‐2,3‐ 3 H‐cyclohexanecarboxylic acid. Preparation of testosterone 17β‐trans‐4‐n‐butyl‐2,3‐ 3 H‐cyclohexanecarboxylate and [4‐ 14 C]‐testosterone 17β‐trans‐4‐n‐butylcyclohexane carboxylate
Author(s) -
Acosta C. K.,
Cessac J. W.,
Rao Pemmaraju N.,
Kim Hyun K.
Publication year - 1990
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.2580281013
Subject(s) - chemistry , cyclohexanecarboxylic acid , diastereomer , tritium , thiourea , cis–trans isomerism , catalysis , medicinal chemistry , stereochemistry , organic chemistry , physics , nuclear physics
The synthesis of trans ‐4‐ n ‐butyl‐2,3‐ 3 H‐cyclohexanecarboxylic acid is described. The title compound was synthesized by catalytic tritiation of 4‐ n ‐butylcyclohex‐2‐enecarboxylic acid, which was obtained from a “double” Birch reduction of 4‐ n ‐butylbenzoic acid. The trans ‐acid was isolated from a mixture of cis/trans diastereomers by the selective formation of a thiourea inclusion complex. The title compound was used for the synthesis of the 17β‐ester of testosterone. In addition, [4‐ 14 C]‐testosterone was esterfied using unlabelled trans acid. The three radiolabelled compounds will be used in metabolism studies.