Water → 17-Methyl-5-alpha-androst-2-en-17-beta-ol

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Reaction Steps

To a solution of compound 2 (300 mg, 1.10 mmol) in anhydrous THF (15 mL) under an atmosphere of argon at 0° C. was added methyl magnesium bromide (1.4 M in THF; 945 μL, 1.32 mmol). The solution was allowed to return to room temperature and was subsequently stirred overnight. The solution was then diluted with ethyl acetate and poured into water. The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude compound was purified by high performance flash chromatography (Biotage) using Hexanes/EtOAc (95:5) as eluant to yield compound 27 (123 mg, 39%). 1H NMR (CDCl3) δ: 0.78 (s, 18-CH3), 0.86 (s, 19-CH3), 1.21 (s, 17α-CH3), 0.65-2.05 (residual CH and CH2), 5.59 (m, 2×CH of alkene).

Provenance & Evidence