Sodium Hydroxide → 4-(Pyridin-4-yl)butan-2-amine

참여 물질

반응 단계

Next, anhydrous ether (19 ml) was added to lithium aluminum hydride (257 mg, 6.77 mmol) under a nitrogen atmosphere, and the mixture was stirred under ice-cooling. A solution of 4-(4-pyridyl)-2-butanone oxime (556 mg, 3.38 mmol) in ether (15 ml) was added dropwise to the mixture over seven minutes, and the whole was stirred at room temperature overnight. Further, the mixture was refluxed for two days and then stirred under ice-cooling. Ethyl acetate was slowly added to the reaction mixture, and then a 1 N aqueous sodium hydroxide solution (slowly at first, total: 20 ml) was added thereto. Chloroform (80 ml) was added thereto, and the resulting insoluble matter was filtered out with Celite. After separation, chloroform in the organic layer was evaporated under reduced pressure. The residue was combined with the aqueous layer, tetrahydrofuran (20 ml) was added thereto, and the whole was stirred at room temperature. Di-t-butyl carbonate (1.48 g, 6.78 mmol) was added thereto. The whole was stirred overnight and extracted with chloroform (50 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. A 4 N solution of hydrogen chloride in ethyl acetate (3 ml) and ethanol (1 ml) were added to the residue, and the whole was stirred at room temperature. After three hours, the reaction mixture was concentrated under reduced pressure, chloroform (5 ml), methanol (5 ml) and triethylamine (1 ml) were added to the residue, the whole was concentrated under reduced pressure, and the residue was purified by basic silica gel column chromatography to give the target compound (161 mg, 32%) as a brown oily matter.

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