ABSTRACT
A new practical synthesis of 17alpha-acetoxy-11beta-(4-N, N-dimethylaminophenyl)-19-norpregna-4,9-diene-3,20-dione (CDB-2914) is described. The synthesis gives easily isolable solids at all steps and is amenable to large-scale process.
Subject(s)
Contraceptives, Postcoital, Synthetic/chemical synthesis , Norpregnadienes/chemical synthesis , Chromatography, Thin Layer/methods , Contraceptives, Postcoital, Synthetic/isolation & purification , Magnetic Resonance Spectroscopy/methods , Norpregnadienes/isolation & purification , Spectroscopy, Fourier Transform Infrared/methodsABSTRACT
The syntheses of N-desmethyl derivatives of CDB-2914 and the mono-N-desmethyl derivative of Mifepristone are described. We also describe the use of the mono-desmethyl derivatives as substrates for the synthesis of N-tritomethyl derivatives of CDB-2914 and Mifepristone with high specific activity (ca. 80 Ci/mmol), which serve as radioligands for radioimmunoassay.
Subject(s)
Mifepristone/chemical synthesis , Norpregnadienes/chemical synthesis , Radioligand Assay , Magnetic Resonance Spectroscopy , Mifepristone/chemistry , Norpregnadienes/chemistry , RadioimmunoassayABSTRACT
Tetrapropylammonium perruthenate N-methylmorpholine N-oxide oxidation of steroidal alcohols is described. The reagent combination is mild and gave good yields of the corresponding ketones. Although the oxidation can generate ketones from 3-, 11-, 15-, 17-, and 20-hydroxy steroids, the oxidation of homoallylic alcohols proceeds in low yields. Finally, we observed that the oxidation reagents will convert 17 alpha-hydroxy-20-keto steroids to 17-keto systems in excellent yield.
