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Synthesis of carbon-13 labeled ibuprofen

✍ Scribed by R. S. P. Hsi; L. S. Stelzer; W. T. Stolle

Publisher
John Wiley and Sons
Year
1989
Tongue
French
Weight
455 KB
Volume
27
Category
Article
ISSN
0022-2135

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✦ Synopsis

This report describes the synthesis of ibuprofen* labeled with carbon-13 either at the terminal methyl carbons, or at the methine carbon of the isobutyl side chain. The synthetic route involves the removal of the isopropyl group in the isobut I side-chain o f ibuprofen via 2-[4-(2-methyl-l-propenyl)phenyl~propionic acid followed by restoration of the isopropyl group with a Wittig' reaction, using appropriate carbon-1 3 labeled acetone as the precursor o f the isopropyl group. Interesting NMR coupling data attributable to phosphorous and carbon-13 are presented in the experimental section.

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