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

HRID 1058374Notes

Reaction equation

HRID 1058374 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 apparatus for 3 h, then the reaction mixture was filtered through Celite® and the filter cake was washed well with methanol (50 mL). The combined filtrates were evaporated under reduced pressure and the residue was dried to constant weight under vacuum to give 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzenemethanamine (950 mg, 95% yield) as an oil.

Workup

  1. filtrationthe reaction mixture was filtered through Celite®
  2. washthe filter cake was washed well with methanol (50 mL)
  3. customThe combined filtrates were evaporated under reduced pressure
  4. customthe residue was dried to constant weight under vacuum

Sources & evidence

ORD record
ord-b08bd525259a462cb028ac23d6a16b8e
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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