Aluminium lithium hydride → 3-(tert-Butyldimethylsiloxymethyl)benzylamine
Reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[C:13]#[N:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH2:13][NH2:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To an ice-cold solution of 3-(tert-butyldimethylsilyloxymethyl)benzonitrile (4.5 g, 18 mmol) in THF (47 mL) was added LiAlH4 (27 mL, of a 1 M solution in THF, 27 mmol), and the reaction mixture was stirred at reflux for 3 h. The reaction mixture was cooled to 0° C., and the reaction was quenched with water (25 mL) and 15% NaOH in water (75 mL). The reaction mixture was filtered, concentrated under reduced pressure, and the residue was dissolved in EtOAc. The organic solution was washed with water and then brine, dried (MgSO4), filtered, and concentrated under reduced pressure to provide 3-(tert-Butyldimethylsilyloxymethyl)benzylamine (1.4 g, 30%) as a clear oil: 1H NMR (300 MHz, CDCl3) δ 7.22-7.10 (m, 4H), 4.57 (s, 2H), 3.74 (s, 2H), 0.84 (s, 9H), 0.09 (s, 6H).
Workup
- temperatureat reflux for 3 h
- customthe reaction was quenched with water (25 mL) and 15% NaOH in water (75 mL)
- filtrationThe reaction mixture was filtered
- concentrationconcentrated under reduced pressure
- dissolutionthe residue was dissolved in EtOAc
- washThe organic solution was washed with water
- dry with materialbrine, dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-041650d08f824e28850d6da66e612d01
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07629363B2
Reaction notes
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