17beta-Formyl-6-t-butylcarboxy-6-azaandrost-4-en-3-one → 17beta-(1-Hydroxy-3-methylbutyl)-6-t-butylcarboxy-6-azaandrost-4-en-3-one

Participants

Reaction Steps

A solution of 17β-formyl-6-t-butylcarboxy-6-azaandrost-4-en-3-one (550 mg, 1.37 mmol), prepared in part B above, in THF (10 mL) is treated with isobutylmagnesium bromide (2.0M in diethyl ether, 2.0 mL, 4.0 mmol) at 0° C. After 20 minutes the reaction is quenched with saturated aqueous NaHSO4, extracted with ethyl acetate (2×40 mL), dried over MgSO4, concentrated and chromatographed on silica gel (50% ethyl acetate/hexanes) to give crude 17β-(1-hydroxy-3-methylbutyl)-6-t-butylcarboxy-6-azaandrost-4-en-3-one of sufficient purity to carry on to the following steps; yield: 168 mg (26%); FAB mass spec. MH+ 460.

Provenance & Evidence