反应详情

Sodium hydride (0.346 g, 8.679 mmol, 60%), washed with hexane and dried with an inert gas, was initially introduced into N,N-dimethylformamide (10 ml) under an inert gas, (1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methanol (1.36 g, 4.34 mmol) was added and the mixture was then stirred at room temperature for 30 min. Triethylamine (1.8 ml, 13.019 mmol) was added, the reaction mixture was cooled with ice-water, and methanesulfonyl chloride (0.838 ml, 10.849 mmol) in N,N-dimethylformamide (10 ml) was slowly added dropwise. After stirring at room temperature for 1 h, 5 ml of water were added and the solvent was removed in vacuo. The residue was taken up in saturated sodium bicarbonate solution (20 ml) and ethyl acetate (50 ml), the phases were separated and the aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phases were washed with saturated sodium chloride solution (40 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with diethyl ether/hexane/methylene chloride (1:1:1). Yield: 1.66 g (97%)

1. customdried with an inert gas
2. additionwas added
3. additionwas slowly added dropwise
4. stirringAfter stirring at room temperature for 1 h
5. customthe solvent was removed in vacuo
6. customethyl acetate (50 ml), the phases were separated
7. extractionthe aqueous phase was extracted with ethyl acetate (2×50 ml)
8. washThe combined organic phases were washed with saturated sodium chloride solution (40 ml)
9. dry with materialdried over sodium sulfate
10. concentrationconcentrated in vacuo
11. customThe crude product was purified by column chromatography (silica gel) with diethyl ether/hexane/methylene chloride (1:1:1)