반응 #9982

반응 방정식

sodium thiosulfate

(±)-1-(t-Butoxycarbonyl)-2-(2-oxo-3-butenyl)pyrrolidine

4-methylthiophenol

sodium hydrogencarbonate

m-chloroperbenzoic acid

→

title compound

수율 94.0%

(±)-1-(t-Butoxycarbonyl)-2-[4-(p-toluenesulfonyl)-2-oxobutyl]pyrolidine

수율 94.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   농축At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
2. 2
   workup.DISSOLUTIONthe resulting residue was dissolved in dichloromethane (2 ml)
3. 3
   workup.STIRRINGthe resulting mixture was stirred at room temperature for 2 hours
4. 4
   추출extracted with dichloromethane
5. 5
   세척The organic layer was washed with water
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   기타the solvent was removed by distillation under reduced pressure

실험 절차

(±)-1-(t-Butoxycarbonyl)-2-(2-oxo-3-butenyl)pyrrolidine (206 mg (10.86 mmol), prepared as described in Reference example 1–2)) was dissolved in tetrahydrofuran (2 ml). To the solution was added 4-methylthiophenol (107 mg, 0.86 mmol), and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the resulting residue was dissolved in dichloromethane (2 ml). To the resulting mixture was added 70 wt % m-chloroperbenzoic acid (468 mg, 1.894 mmol) by portions under ice cooling, and the resulting mixture was stirred at room temperature for 2 hours. To the mixture were added an aqueous solution of 10% sodium thiosulfate and a saturated aqueous solution of sodium hydrogencarbonate in that order, and the resulting mixture was stirred and extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure, to give the title compound (322 mg) as a colorless oil (yield 94%).

출처