tert-Butanol → 1-Benzyl-3-(tritylamino)-2-azepanone

Participants

Reaction Steps

To a suspension of 3-(tritylamino)-2-azepanone (2.85 g, 7.69 mmol) in tetrahydrofuran (30 ml) was added 60%-sodium hydride (462 mg, 11.6 mmol) at 0° C., and then stirred at room temperature for 30 minutes. Subsequently, a solution of benzyl bromide (1.0 ml, 8.41 mmol) in tetrahydrofuran (5 ml) was added dropwise thereto at room temperature over a period of 3 minutes, followed by adding thereto tetra-n-butylammonium iodide (57 mg, 0.15 mmol), and the resulting mixture was stirred at room temperature for 6 hours. The reaction mixture was cooled on an ice-water bath and t-butanol (0.7 ml) and water (1 ml) were added thereto at 0° C. The resulting mixture was poured into water and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: n-hexane/chloroform) to obtain 1-benzyl-3-(tritylamino)-2-azepanone (2.22 g, 63%).

Provenance & Evidence