m-Chloroperbenzoic acid → (S)-5-bromo-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-2,7-dimethylquinoline 1-oxide

Participants

Reaction Steps

To a solution of (S)-ethyl 2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyacetate (5H) (500 mg, 1.27 mmol) in dichloromethane (13 mL) at 0° C. was added 3-chloroperoxybenzoic acid (269 mg, 77%, 1.21 mmol) and the reaction mixture was allowed to slowly warm to room temperature over 3 hours. The reaction mixture was partitioned between ethyl acetate and water and the organic layer was concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes and methanol/ethyl acetate) to give a yellow oil (497 mg, 95%). LCMS-ESI+ (m/z): [M]+ calcd for C19H2413rNO4: 410.3;

Provenance & Evidence