3-{[tert-Butyl(dimethyl)silyl]oxy}benzonitrile → 3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]benzenemethanamine

HRID 1352003Notes

Reaction equation

HRID 1352003 reaction equation
[CH3:1][C:2]([Si:5]([CH3:16])([CH3:15])[O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11])([CH3:4])[CH3:3]>[Pd].CO>[CH3:4][C:2]([Si:5]([CH3:16])([CH3:15])[O:6][C:7]1[CH:8]=[C:9]([CH2:10][NH2:11])[CH:12]=[CH:13][CH:14]=1)([CH3:1])[CH3:3]

Participants

4

Reactant 1

HCID 226614893-{[tert-Butyl(dimethyl)silyl]oxy}benzonitrile

Product 1

HCID 222661693-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]benzenemethanamineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under an atmosphere of nitrogen, 10% palladium on carbon (250 mg) was added to a solution of 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzonitrile (1 g, 4.3 mmol) in methanol (25 mL) at 25° C. The reaction mixture was hydrogenated at 50 psi in a Parr shaker for 3 h. The reaction mixture was then filtered through Celite and the filter cake was washed well with methanol (50 mL). The solvents were concentrated under reduced pressure and the residue was dried under vacuum for 1 h to give 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-benzenemethanamine (950 mg, 95%) as an oil.

Workup

  1. filtrationThe reaction mixture was then filtered through Celite
  2. washthe filter cake was washed well with methanol (50 mL)
  3. concentrationThe solvents were concentrated under reduced pressure
  4. customthe residue was dried under vacuum for 1 h

Sources & evidence

ORD record
ord-b5458e00b8c1475593daf6bf1b6a1828
Source dataset
uspto-grants-2007_05
Patent number
US07217728B2

Reaction notes

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