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Published on: September 21, 2019
A concise method for the preparation of deuterium-labeled cortisone: synthesis of [6,7-2H]cortisone
Agnieszka Sulima1, Thomas E Prisinzano, Thomas Spande
1Laboratory of Medicinal Chemistry, Building 8, Room B1-23, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, 8 Center Drive MSC 0815, Bethesda, MD 20892, USA.
Abstract:
A method is described for the synthesis of isotopically labeled cortisone from commercially available cortisone acetate through a Delta(4,6)-dieneone. Direct deuteration of the dienone acetate with various catalysts in different solvent systems failed to give an isolable product. Initial hydrolysis of the side-chain ester of the Delta(4,6)-dieneone and subsequent derivatization gave the key intermediate, 17alpha,20;20,21-bismethylenedioxy-pregna-4,6-diene-3,11-dione, which could be satisfactorily deuterated to the desired product. The availability of [6,7-(2)H]cortisone will provide a tool for the future study of the metabolism of cortisone in human tissues.
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