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

HRID 1726714Notes

Reaction equation

HRID 1726714 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-ce949c4aab07440382ecd348b3de38e1
Source dataset
uspto-grants-2009_02
Patent number
US07491741B2

Reaction notes

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