Water → (2beta,3alpha,5alpha,17beta)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstane-17-carbonitrile

Temperature

135 °C

2,2-Dimethylmorpholine hydrochloride (2.43 g) and sodium hydroxide (640 mg) were added to a mixture of (2α,3α,5α,17β)-2,3-epoxyandrostane-17-carbonitrile (1.2 g) (prepared as described in British patent 1,434,919) in 1,2-ethanediol (12 ml) and the mixture was heated at 135° C. in an atmosphere of nitrogen for 24 h. The reaction mixture was poured into water (100 ml) and the precipitated solid was filtered off and then dissolved in dichloromethane. The solution was washed with water and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue (1.55 g) was chromatographed on silica gel. The purified product (1.18 g) was crystallised from ether-heptane to give (2β,3α,5α,17β)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstane-17-carbonitrile (903 mg). m.p. 170°-173° C.; [α]D +117.5° (c 0.8).

1. filtrationthe precipitated solid was filtered off
2. dissolutiondissolved in dichloromethane
3. washThe solution was washed with water
4. dry with materialdried over sodium sulfate
5. customThe solvent was removed under reduced pressure
6. customthe residue (1.55 g) was chromatographed on silica gel
7. customThe purified product (1.18 g) was crystallised from ether-heptane

ORD record

ord-1f3f1e68229445159021e9436acee179

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05593983