Efficient oxidizing methods for the synthesis of oxandrolone intermediates.
Mild, efficient and eco-friendly oxidation of 17alpha-methylandrostan-3beta-17beta-diol (1) has been studied with three different reagents viz. pentavalent iodine reagent 2-iodoxy benzoic acid (IBX) in DMSO at 65 degrees C, sodium hypochlorite and H2O2/Na2WO4 under phase transfer conditions to give 17beta-hydroxy-17alpha-methylandrostan-3-one (mestanolone 2), a drug intermediate as oxidized product. The H2O2/Na2WO4/PTC gave mestanolone in high yield and purity whereas sodium hypochlorite/PTC system yielded some chlorinated material along with the mestanolone. However, 1 with 2.5 equivalent of IBX gave 17beta-hydroxy-17alpha-methyl-Delta1-androsten-3-one (3) under the similar reaction conditions in good yield and single step reaction.
Ginotra
Sandeep K
SK
Medicinal Chemistry Research Laboratory, Dr. B. R. Ambedkar Center for Biomedical Research, University of Delhi, Dehli, India.
Chhikara
Bhupender S
BS
Singh
Manish
M
Chandra
Ramesh
R
Tandon
Vibha
V
D015113:Androstane-3,17-diol / Q000737:chemistry*; D019817:Benzoic Acid / Q000737:chemistry; D002713:Chlorine / Q000737:chemistry; D013196:Dihydrotestosterone / Q000031:analogs & derivatives* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry; D008956:Models, Chemical; D010074:Oxandrolone / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D012973:Sodium Hypochlorite / Q000737:chemistry
D013196:Dihydrotestosterone; D015113:Androstane-3,17-diol; D002713:Chlorine; D010074:Oxandrolone; D019817:Benzoic Acid; D007455:Iodine; D012973:Sodium Hypochlorite; C008376:mestanolone