반응 #9983

반응 방정식

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

hydrochloric acid dioxane

→

title compound

수율 65.3%

(±)-1,2,3,5,6,7,8,8a-Octahydroindolizin-7-one

수율 65.3%

용매

methanol

반응 조건

후처리

1. 1
   농축At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
2. 2
   기타to remove solvents
3. 3
   workup.ADDITIONTo the residue was added a saturated aqueous solution of sodium hydrogencarbonate
4. 4
   추출this was extracted 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
8. 8
   기타The residue was purified by column chromatography through alumina (eluent, ethyl acetate)

실험 절차

(±)-1-(t-Butoxycarbonyl)-2-[4-(p-toluenesulfonyl)-2-oxobutyl]pyrrolidine (322 mg (0.814 mmol), prepared as described in 1)) was dissolved in methanol (3.2 ml). To the solution was added a solution of 4N hydrochloric acid/dioxane (0.61 ml, 2.44 mmol), and the resulting mixture was stirred at 50° C. for 30 minutes. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure to remove solvents and any excess of hydrochloric acid. To the residue was added a saturated aqueous solution of sodium hydrogencarbonate and this was 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. The residue was purified by column chromatography through alumina (eluent, ethyl acetate), to give the title compound (74 mg) as a light brown oil (yield 65%).

출처