Reaktion #9983

Reaktionsgleichung

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

hydrochloric acid dioxane

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title compound

Ausbeute 65.3%

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

Ausbeute 65.3%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

(±)-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%).

Quelle