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Synthesis of dexamethasone labeled with carbon‐14 and tritium
Author(s) -
Mertel H. E.,
Gerber A. M.,
Meriwether H. T.
Publication year - 1970
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.2590060305
Subject(s) - tritium , chemistry , halogenation , steroid , dexamethasone , radiochemistry , carbon fibers , methyl iodide , catalysis , carbon 14 , organic chemistry , medicinal chemistry , hormone , biochemistry , materials science , physics , medicine , quantum mechanics , composite number , nuclear physics , composite material
The syntheses of dexamethasone‐16α‐(methyl)‐ 14 C and dexamethasone‐16β‐ 3 H are described. Tritium labeling was achieved by catalytic addition of tritium to 3‐acetoxypregn‐16‐ene‐11,20‐dione, followed by bromination and dehydrobromination to give 3α‐acetoxy‐16‐ 3 H‐pregn‐16‐ene‐11, 20‐dione. The stereochemistry of this sequence of reactions has been studied in detail. Carbon‐14 was introduced into the steroid nucleus by reaction of methyl‐ 14 C‐magnesium iodide with 3α‐acetoxypregn‐16‐ene‐11,20‐dione. These tritium and carbon‐14 labeled intermediates were then carried through to the corresponding labeled dexamethasone by parallel reaction sequences.