反应详情

A solution of tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(pyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate (1.15 g, 2.127 mmol) in DCM (22 mL) was cooled to 0° C. and m-CPBA (0.953 g, 4.25 mmol) was added. The reaction was warmed to room temperature. After 2 hours the reaction was quenched with aqueous sodium bisulfite (20 mL). The reaction was then diluted with EtOAc (150 mL) and washed vigorously with aqueous sodium bisulfite (3×40 mL). The organics were washed with brine (2×40 mL), saturated aqueous NaHCO3 (3×40 mL) and then brine (2×40 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to afford tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(1-oxidopyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate (1.18 g, 100%). LC-MS=557.2 (M+1)+.

1. customAfter 2 hours the reaction was quenched with aqueous sodium bisulfite (20 mL)
2. additionThe reaction was then diluted with EtOAc (150 mL)
3. washwashed vigorously with aqueous sodium bisulfite (3×40 mL)
4. washThe organics were washed with brine (2×40 mL), saturated aqueous NaHCO3 (3×40 mL)
5. dry with materialThe organic layer was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated