반응 #5166

반응 방정식

1-bromo-2-fluoroethane

sodium iodide

sodium bicarbonate

(2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine

sodium bicarbonate

→

(2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-1-(2-fluoroethyl)pyrrolidine

용매

dimethylformamide

반응 조건

후처리

1. 1
   온도cooling
2. 2
   workup.WAITat 40° C. for 20 hours
3. 3
   추출extracted with ethyl acetate
4. 4
   세척The extract was washed with a saturated aqueous solution of sodium chloride
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   기타The solvent was then removed by distillation under reduced pressure
7. 7
   기타melting of 122°-123° C.
8. 8
   기타were obtained as a powder from those fractions
9. 9
   세척eluted with ethyl acetate

실험 절차

0.4 ml of 1-bromo-2-fluoroethane, 3.83 g of sodium iodide and 0.38 g of sodium bicarbonate were added to a solution of 1.2 g of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 12 ml of dry dimethylformamide, whilst ice-cooling, and the mixture was stirred at room temperature for 20 minutes and then at 40° C. for 20 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was subjected to column chromatography through silica gel (Katayama Chemicals Industries Co., silica gel 60K070). 838 mg of the title compound, melting of 122°-123° C., were obtained as a powder from those fractions eluted with ethyl acetate.

출처