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

Lithium aluminum hydride (299 mg, 7.87 mmol) was suspended in anhydrous diethyl ether (10 ml) under a nitrogen atmosphere, and 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. The temperature was raised to room temperature, and the mixture was stirred for 75 minutes. The reaction mixture was cooled with ice, ethyl acetate (15 ml) was added to the reaction mixture, and water (0.28 ml), a 15% aqueous sodium hydroxide solution (0.28 ml) and water (0.85 ml) were added thereto successively. The temperature was raised to room temperature, and the whole was stirred 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 titled compound (180.0 mg, yellow oily matter, 17.8%).

1. temperaturecooling
2. stirringthe mixture was stirred for 75 minutes
3. temperatureThe temperature was raised to room temperature
4. stirringthe whole was stirred for 10 minutes
5. dry with materialThe reaction mixture was dried over anhydrous magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. customthe residue was purified by silica gel column chromatography

ORD-Eintrag

ord-c063087050384aefa89497c908e8c7af

Quelldatensatz

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07923461B2