Hydrogen Peroxide → HCID 22872556, compound

Participants

Reaction Steps

Borane-tetrahydrofurancomplex (0.68 mL, 0.68 mmol) was added to a solution of (3β,25R)-3-ethoxymethoxy-5-spirostene (0.10 g, 0.21 mmol) in tetrahydrofuran (8 mL). The mixture was stirred under nitrogen atmosphere at ambient temperature for 3.5 hours. The reaction mixture was cooled to 0° C. and methanol (1.5 mL), 15% sodium hydroxide solution (1.5 mL) and 30% hydrogen peroxide (1.5 mL) were added. The reaction mixture was then gradually warmed to ambient temperature and stirred overnight. The reaction was quenched at 0° C. by the addition of saturated sodium bisulfite solution. The mixture was diluted with ethyl acetate and washed with ammonium chloride solution (1x), brine (1x), dried (sodium sulfate), filtered and concentrated in vacuo to give 0.11 g of a mixture of the 6α-alcohol and the 6β-alcohol. The two products were separated by flash chromatography on silica gel (6:4 hexane/ethyl acetate). The major product (Rf=0.40) was identified to be the title compound.

Provenance & Evidence