Acetone → (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyacetic acid

Participants

Reaction Steps

To a stirred solution of (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethanol (38 g, 108 mmol) in acetone (500 mL) was added RuCl3.3H2O (2.83 g, 10.83 mmol) followed by NaIO4 (116 g, 540 mmol) in H2O (400 mL) at 0° C. The mixture was stirred at room temperature for 2 hours. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product. LCMS-ESI+: calc'd for C17H20BrNO3: 366.1 (M+H+); Found: 366.0 (M+H+).

Provenance & Evidence