Hydrogen Peroxide → HCID 22872556, compound

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 (1×), brine (1×), 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.

1. temperatureThe reaction mixture was cooled to 0° C.
2. temperatureThe reaction mixture was then gradually warmed to ambient temperature
3. stirringstirred overnight
4. customThe reaction was quenched at 0° C. by the addition of saturated sodium bisulfite solution
5. additionThe mixture was diluted with ethyl acetate
6. washwashed with ammonium chloride solution (1×), brine (1×)
7. dry with materialdried (sodium sulfate)
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-26b9257e6aac4573860ab4ba7dc3a354

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05703052