Toluene → HCID 69828311, compound

Participants

Reaction Steps

Prepare M82 by treating a solution of M81 in DMF with t-butyldimethylsilyl chloride following the procedure described in example 13a. To a solution of 3β-[[(1,1-dimethylethyl)dimethylsilyl]oxy]androst-5,15-dien-17-one (M82) (10.0 g, 24.96 mmol) and cuprous bromide (71.5 mg, 0.5 mmol) dissolved in tetrahydrofuran (100 mL) under a nitrogen atmosphere, add a 2M solution of tri-methylaluminum in toluene (13.8 mL, 27.6 mmol). Add trimethylsilyl chloride (5.88 g, 54 mmol) dropwise to the solution. After 2 hours, add water (5 mL) cautiously. Remove the solids by filtration and wash. Purify the crude product by flash chromatography to give 3β-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-15α-methylandrost-5-en-17-one (N88a).

Provenance & Evidence