Reaktion #320708

Reaktionsgleichung

water

2,2-Dimethylmorpholine hydrochloride

sodium hydroxide

(2α,3α,5α,17β)-2,3-epoxyandrostan-11-one-17-carbonitrile

→

(2β,3α,5α,17β)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstan-11-one-17-carbonitrile

Lösungsmittel

1,2-ethanediol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe precipitated solid was filtered off
2. 2
   workup.DISSOLUTIONdissolved in dichloromethane
3. 3
   WaschenAfter washing the solution with water
4. 4
   Trocknendrying over sodium sulfate
5. 5
   Sonstigethe solvent was removed under reduced pressure
6. 6
   Sonstigethe residue (6.9 g) was chromatographed on silica gel
7. 7
   SonstigeThe purified product (4.3 g) was sequentially crystallised from ethanol and acetone-diethyl ether

Vorschrift

2,2-Dimethylmorpholine hydrochloride (9.67 g) and sodium hydroxide (2.55 g) were added to a mixture (4:1) of (2α,3α,5α,17β)-2,3-epoxyandrostan-11-one-17-carbonitrile and its 3α,4α-epoxy isomer (5.0 g) (British patent 1,434,919) in 1,2-ethanediol (50 ml) and the mixture was heated in an atmosphere of nitrogen at 120° C. for 19 h and then at 150° C. for 4.5 h. The reaction mixture was poured into water (500 ml) and the precipitated solid was filtered off and dissolved in dichloromethane. After washing the solution with water and drying over sodium sulfate, the solvent was removed under reduced pressure and the residue (6.9 g) was chromatographed on silica gel. The purified product (4.3 g) was sequentially crystallised from ethanol and acetone-diethyl ether to give (2β,3α,5α,17β)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstan-11-one-17-carbonitrile (2.37 g). m.p. 206°-210° C.; [α]D +122.9° (c 0.8).

Quelle