Hydrochloric Acid → HCID 25142566, compound

Aqueous HCl (1 M, 20 mL) was added to a suspension of 3α-(t-butyldimethylsiloxy)-17β-nitro-5α-androstane (2.89 g, 6.6 mmol) in methanol (100 mL) and was allowed to stir overnight at room temperature. The reaction mixture was concentrated under reduced pressure, partitioned between EtOAc (100 mL) and brine (50 mL), and the layers were separated. The aqueous fraction was then extracted with EtOAc (2×50 mL) and the organic extracts were combined, washed with saturated aqueous NaHCO3 (50 mL), brine (50 mL), dried over (Na2SO4), and concentrated under reduced pressure. The resulting semisolid was purified on silica using medium pressure column chromatography (hexane/EtOAc, 7:3) to provide 17β-nitro-5α-androstan-3α-ol (1.05 g, 49%) as a pale yellow solid. 1H-NMR (300 MHz, CDCl3) δ 0.73 (s, 3H), 0.79 (s, 3H), 2.05-0.86 (m, 23H), 2.70-2.52 (m, 1H), 4.05 (br s, 1H), 4.37 (dd, J=9, 9 Hz, 1H).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. custompartitioned between EtOAc (100 mL) and brine (50 mL)
3. customthe layers were separated
4. extractionThe aqueous fraction was then extracted with EtOAc (2×50 mL)
5. washwashed with saturated aqueous NaHCO3 (50 mL), brine (50 mL)
6. dry with materialdried over (Na2SO4)
7. concentrationconcentrated under reduced pressure
8. customThe resulting semisolid was purified on silica using medium pressure column chromatography (hexane/EtOAc, 7:3)

ORD record

ord-4d5005a5d3bb4ada839613bbf1054195

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575375B2