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 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.

Provenance & Evidence