Water → 1-(2-Amino-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)pentan-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-N-methylbenzamide (4.97 g, 16.0 mmol) in tetrahydrofuran (50 ml) was added dropwise slowly 1.6 M solution (20 ml) of n-butyllithium in n-hexane at −78° C., and after the completion of the dropwise addition, the mixture was stirred at −78° C. for 30 min. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give 1-(2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)pentan-1-one (3.45 g, yield 70%) as a pale-yellow oil.

Provenance & Evidence