반응 #320676

반응 방정식

sodium carbonate

N-Chlorosuccinimide

(2β,3α,5α)-3-hydroxy-20-[(2-hydroxyethyl)imino]-2-(2,2-dimethyl-4-morpholinyl)pregnan-11-one

hydrochloric acid

→

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

용매

tetrahydrofuran

water

반응 조건

후처리

1. 1
   workup.STIRRINGAfter stirring at room temperature for 1.25 h
2. 2
   여과the precipitated solid was filtered off
3. 3
   세척washed with water
4. 4
   workup.DISSOLUTIONdissolved in dichloromethane
5. 5
   건조After drying over sodium sulfate
6. 6
   기타the solvent was removed under reduced pressure
7. 7
   기타the residue was chromatographed on silica gel
8. 8
   기타The purified product was crystallised from diethyl ether

실험 절차

N-Chlorosuccinimide (2.16 g) was added to a solution of (2β,3α,5α)-3-hydroxy-20-[(2-hydroxyethyl)imino]-2-(2,2-dimethyl-4-morpholinyl)pregnan-11-one (8.77 g) in tetrahydrofuran (175 ml). The solution was stirred at room temperature for 2 h and hydrochloric acid (53 ml; 1M) was then added. After stirring at room temperature for 1.25 h, the reaction mixture was poured into water (1 l). The pH was adjusted to 9 with aqueous sodium carbonate and the precipitated solid was filtered off, washed with water and dissolved in dichloromethane. After drying over sodium sulfate, the solvent was removed under reduced pressure and the residue was chromatographed on silica gel. The purified product was crystallised from diethyl ether to give (2β,3α,5α)-21-chloro-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione (3.23 g). m.p. 206°-208° C. (dec); [α]D +130.5° (c 0.57).

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