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

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Reaction Steps

A solution of 17β-(1-hydroxy-3-methylbutyl)-6-t-butylcarboxy-6-azaandrost-4-en-3-one (160 mg, 0.349 mmol) prepared in part C above, in DMF (10 mL) is treated with pyridinium dichromate (656 mg, 1.74 mmol) at room temperature. After 10 hrs the reaction is poured into water, extracted with ethyl acetate (2×50 mL), the extracts are dried over MgSO4, concentrated and chromatographed on silica gel (40% ethyl acetate/hexanes) to give crude 17β-(1 -oxo-3-methylbutyl)-6-t-butylcarboxy-6-azaandrost-4-en-3-one; yield: 135 mg (85%). A portion of this material (81 mg, 0.18 mmol) is treated with trifluoroacetic acid as described in Example 4 above to give, after recrystallization from diethyl ether/hexanes 17β-(1-oxo-3-methylbutyl)-6-azaandrost-4-en-3-one as a white crystalline solid; yield: 58 mg (92%); m.p. 169°-171° C. Anal. Calcd. for C23H35NO2 ·1/4H2O; C, 76.30; H, 9.88; N, 3.87. Found: C, 76.48; h, 9.93; N, 3.89.

Provenance & Evidence