Reaktion #320704

Reaktionsgleichung

(2β,3α,5α)-21-chloro-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione

sodium cyanide

N,N-dimethylformamide

→

(2β,3α,5α)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)-11,20-dioxopregnane-21-carbonitrile

Lösungsmittel

water

methanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 16 h
3. 3
   TemperaturThe resulting solution was cooled
4. 4
   ExtraktionThe mixture was extracted with dichloromethane
5. 5
   Waschenthe organic layer was washed with water to pH 7
6. 6
   TrocknenAfter drying the solution over sodium sulfate
7. 7
   Sonstigethe solvent was removed under reduced pressure
8. 8
   Sonstigethe residue (430 mg) was chromatographed on silica gel
9. 9
   SonstigeThe purified product (208 mg) was crystallised from dichloromethane-methanol

Vorschrift

A stirred mixture of (2β,3α,5α)-21-chloro-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione (500 mg), sodium cyanide (500 mg), N,N-dimethylformamide (1.25 ml) in methanol (10 ml) and water (0.25 ml) was heated under reflux for 16 h. The resulting solution was cooled and poured into water (50 ml). The mixture was extracted with dichloromethane and the organic layer was washed with water to pH 7. After drying the solution over sodium sulfate, the solvent was removed under reduced pressure and the residue (430 mg) was chromatographed on silica gel. The purified product (208 mg) was crystallised from dichloromethane-methanol to give (2β,3α,5α)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)-11,20-dioxopregnane-21-carbonitrile (96 mg). δ (CDCl3) 0.62 (s, 3H), 1.06 (s,3H), 1.22 (s,3H), 1.26 (s,3H) and 3.38 (s,2H).

Quelle