Water → HCID 54140085, compound

A portion (4.0 g) of the solid (A) of Example 31 was dissolved in ethanol (140 ml) and sodium (8.5 g) was added portionwise over 4 h. The mixture was poured into water (1.4 l) and the precipitated solid was filtered off, washed with water and dissolved in methanol (40 ml). Methanesulfonic acid (1.6 ml) was added and the solution was stirred at room temperature for 1 h and then poured into water (400 ml). After extraction with ethyl acetate, sodium carbonate was added to the aqueous phase until the pH exceeded 9. The resulting mixture was extracted with dichloromethane and the organic phase was washed with water. After drying over sodium sulfate, the solvent was removed under reduced pressure and the residue was chromatographed on silica gel. The purified product was crystallised from diethyl ether to give (2β,3α,5α,11α)-3,11-dihydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnan-20-one (750 mg). m.p. 182°-185° C.; [α]D +125.6° (c 0.25).

1. filtrationthe precipitated solid was filtered off
2. washwashed with water
3. dissolutiondissolved in methanol (40 ml)
4. additionMethanesulfonic acid (1.6 ml) was added
5. additionpoured into water (400 ml)
6. extractionAfter extraction with ethyl acetate, sodium carbonate
7. additionwas added to the aqueous phase until the pH
8. extractionThe resulting mixture was extracted with dichloromethane
9. washthe organic phase was washed with water
10. dry with materialAfter drying over sodium sulfate
11. customthe solvent was removed under reduced pressure
12. customthe residue was chromatographed on silica gel
13. customThe purified product was crystallised from diethyl ether

ORD record

ord-7d03e44034e545bdbd5ef9e2b8f9b071

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05593983