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 (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.

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 (1x), brine (1x)
7. dry with materialdried (sodium sulfate)
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-586ec90a8625436a853e015448400667

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05629295