Реакция #9983

Уравнение реакции

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

hydrochloric acid dioxane

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title compound

Выход 65.3%

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

Выход 65.3%

Растворители

methanol

Условия реакции

Обработка

1. 1
   КонцентрированиеAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
2. 2
   Другоеto remove solvents
3. 3
   workup.ADDITIONTo the residue was added a saturated aqueous solution of sodium hydrogencarbonate
4. 4
   Экстракцияthis was extracted with dichloromethane
5. 5
   ПромывкаThe organic layer was washed with water
6. 6
   Сушкаdried over anhydrous magnesium sulfate
7. 7
   Другоеthe solvent was removed by distillation under reduced pressure
8. 8
   ДругоеThe residue was purified by column chromatography through alumina (eluent, ethyl acetate)

Методика

(±)-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%).

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