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

Participants

Reaction Steps

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.

Provenance & Evidence