反応 #9983

反応方程式

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

hydrochloric acid dioxane

→

title compound

収率 65.3%

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

収率 65.3%

溶媒

methanol

反応条件

後処理

1. 1
   濃縮At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
2. 2
   その他to remove solvents
3. 3
   workup.ADDITIONTo the residue was added a saturated aqueous solution of sodium hydrogencarbonate
4. 4
   抽出this was extracted with dichloromethane
5. 5
   洗浄The organic layer was washed with water
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   その他the solvent was removed by distillation under reduced pressure
8. 8
   その他The residue was purified by column chromatography through alumina (eluent, ethyl acetate)

実験手順

(±)-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%).

出典