반응 #320708

반응 방정식

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

용매

1,2-ethanediol

반응 조건

후처리

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

실험 절차

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).

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