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

HRID 2075895

Reaction equation

HRID 2075895 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]([CH:25]([C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)[CH2:26][C:27]#[N:28])[Si:8]([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OCC)(=O)C.[OH-].[Na+]>C(OCC)C.O>[Si:8]([O:7][CH:25]([C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)[CH2:26][CH2:27][NH2:28])([C:21]([CH3:23])([CH3:24])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 219742193-(t-Butyldiphenylsiloxy)-3-(4-pyridyl)propionitrile

Product 1

HCID 121366443-(t-Butyldiphenylsilyloxy)-3-(4-pyridyl)propylamineYield 17.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-c063087050384aefa89497c908e8c7af
Source dataset
uspto-grants-2011_04
Patent number
US07923461B2

Linked notes

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