Patent ID: 7071328

Claim:
A method of preparing 21-hydroxy-6,19-oxidoprogesterone (1) or an acyl or phosphate derivative thereof. the method comprising a) protecting the C-3 hydroxy group of 21-acetoxypregnenolone through formation of a labile ester; b) obtaining the bromohydrin product thereof, by addition of a bromine and a hydroxy group onto the double bond of position of C5-C6 of the ester protected 21-acetoxy-pregnenolone; c) performing an intramolecular cyclization with the C19 atom with the “Suarez-reagent” (diacetoxyiodobenzene) and iodine under irradiation, thus obtaining the 6,19 oxido-bridge within the scaffold; d) performing a selective hydrolysis, followed by an oxidation, to obtain a bromo-ketone; e) performing a hydrolysis of the bromoketone resulting from step d) to obtain 21-hydroxy-6,19-oxidoprogesterone (1); and optionally f) reacting compound (1) with an acylating agent or phosphorylating agent.