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Preparation of cholesterol‐25‐ 3 H
Author(s) -
Joly Raymond A.,
Sauer Horst H.,
Bonner James
Publication year - 1969
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.2590050112
Subject(s) - tritium , grignard reaction , iodide , chemistry , cholesterol , radiochemistry , organic chemistry , nuclear chemistry , medicinal chemistry , biochemistry , physics , reagent , nuclear physics
The synthesis of cholesterol‐25‐ 3 H ( 9 ) described here starts with the readily available 3β‐hydroxy‐δ 5 ‐cholenic acid ( 1 ). The acetate of this acid was converted to the next higher homolog by the Arndt‐Eistert method. Grignard reaction with methyl iodide gave 25‐hydroxycholesterol ( 6 ), which was then brominated. Tritium was finally introduced by treating the 25‐bromocholesterol ( 8 ) with LiAl 3 H 4 .