反应详情

To a stirred solution of tert-butyl 4-[3-(ethoxycarbonyl)phenyl]piperidine 1-carboxylate (48 g, 220 mmol) in chloroform (900 mL) was added ruthenium (IV) oxide hydrate (6.0 g, 45 mmol) followed by a solution of sodium periodate (150 g, 700 mmol) in water (900 m L). The resulting heterogenous reaction mixture was stirred at room temperature for 11 days before being filtered through a short column of celite. The organic layer was removed and the aqueous layer was extracted twice with DCM. The combined organic layers were washed with a 10% solution of sodium thiosulfate in water twice, and once with brine. This solution was dried over MgSO4, filtered, and concentrated under reduced pressure. The product was purified by flash chromatography (silica gel, 20% EA/hexanes) to give 22.5 g (64.8 mmol) of tert-butyl 4-[3-(ethoxycarbonyl)phenyl]-2-oxopiperidine-1-carboxylate (29%).

1. filtrationbefore being filtered through a short column of celite
2. customThe organic layer was removed
3. extractionthe aqueous layer was extracted twice with DCM
4. washThe combined organic layers were washed with a 10% solution of sodium thiosulfate in water twice
5. dry with materialThis solution was dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe product was purified by flash chromatography (silica gel, 20% EA/hexanes)