Ethyl Acetate → 3-(t-Butyldiphenylsilyloxy)-3-(4-pyridyl)propylamine

Participants

Reaction Steps

Lithium aluminum hydride (299 mg, 7.87 mmol) was suspended in anhydrous diethyl ether (10 ml) under a nitrogen atmosphere, a solution of the obtained 3-(t-butyldiphenylsiloxy)-3-(4-pyridyl)propionitrile (1.00 g, 2.59 mmol) in anhydrous diethyl ether (15 ml) was added dropwise to the suspension under ice-cooling with stirring over eight minutes, and the mixture was stirred at room temperature for 75 minutes. Ethyl acetate (15 ml) was added to the reaction mixture under ice-cooling, water (0.28 ml), a 15% aqueous sodium hydroxide solution (0.28 ml) and water (0.85 ml) were added thereto successively, and the whole was stirred at room temperature for 10 minutes. The reaction mixture was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the target compound (180.0 mg, yellow oily matter, 17.8%).

Provenance & Evidence