Benzyl Bromide → 17beta-(Tert-butyldimethylsilyloxy)-7alpha-(3-(3-benzyloxy-5-hydroxyphenyl)propyl)-5alpha-androstan-3-one

Participants

Reaction Conditions

Reaction Steps

17β-(tert-Butyldimethylsilyloxy)-7α-(3-(3,5-dihydroxyphenyl)propyl)-5α-androstan-3-one (75 mg), benzyl bromide (16.9 μl) and potassium carbonate (56 mg) were suspended in DMF (1 ml) and stirred overnight at 25° C. After addition of saturated aqueous ammonium chloride, the reaction mixture was extracted with ethyl acetate and then washed with water and saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and then filtered. After evaporation under reduced pressure to remove the solvent, the resulting residue was subjected to silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/4) to give 17β-(tert-butyldimethylsilyloxy)-7α-(3-(3-benzyloxy-5-hydroxyphenyl)propyl)-5α-androstan-3-one (21.0 mg, yield 24%).

Provenance & Evidence