反应详情

To a solution of lithium hydroxide monohydrate (316 mg) in water (10 ml) was added dropwise a 30 wt % aqueous solution of hydrogen peroxide (1.8 ml) under ice-cooling and the mixture was stirred for 10 minutes. To this reaction solution was added tetrahydrofuran (10 ml), and then a solution of the low-polarity component of 5-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-1-(2,4-dimethoxybenzyl)piperidin-2-one (3.37 g) in tetrahydrofuran (20 ml) was added dropwise thereto, and the mixture was stirred for additional 1 hour. To this reaction solution was added an aqueous solution of sodium hydrogen sulfite (1.81 g) was added dropwise, and then the mixture was warmed to room temperature, and stirred for 30 minutes. This mixed solution was extracted with ethyl acetate, and the resulting organic layer was washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To the resulting residue was added ethyl acetate, and the mixture was stirred at room temperature. The insoluble substance was collected by filtration, and dried under reduced pressure to give the titled compound (1.36 g). An analysis of this solid by HPLC analysis condition 2 showed that an isomer with shorter retention time was a main product.

1. temperaturecooling
2. stirringthe mixture was stirred for additional 1 hour
3. additionwas added dropwise
4. stirringstirred for 30 minutes
5. extractionThis mixed solution was extracted with ethyl acetate
6. washthe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. additionTo the resulting residue was added ethyl acetate
10. stirringthe mixture was stirred at room temperature
11. filtrationThe insoluble substance was collected by filtration
12. customdried under reduced pressure