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.
Medicinal Chemistry Research Laboratory, Dr. B. R. Ambedkar Center for Biomedical Research, University of Delhi, Dehli, India.
Sandeep K
SK
Ginotra
Bhupender S
BS
Chhikara
Manish
M
Singh
Ramesh
R
Chandra
Vibha
V
Tandon
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