反应详情

To a mixture of 0.150 g (0.54 mmole) of (rac)-(3R,4R)-4-azido-3-hydroxy-piperidine-1-carboxylic acid benzyl ester in 3.75 mL of tetrahydrofuran-dimethylformamide (4:1) at 0 degrees, was added 0.026 g of sodium hydride (60% mineral oil dispersion). After stirring for 10 minutes, 0.060 mL of iodomethane was added. The mixture was warmed to room temperature, stirred for 2 hours, then cooled in an ice-bath, and 1 mL of saturated aqueous ammonium chloride solution added. The resulting mixture was partitioned between 50 mL of ethyl acetate and 50 mL of saturated aqueous ammonium chloride solution. The organic layer was successively with water, then brine and dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatoraphy, eluting with hexanes-ethyl acetate (85:15) to give 0.085 g of (rac)-(3R,4R)-4-azido-3-methoxy-piperidine-1-carboxylic acid benzyl ester as a colorless oil.

1. stirringstirred for 2 hours
2. temperaturecooled in an ice-bath
3. customThe resulting mixture was partitioned between 50 mL of ethyl acetate and 50 mL of saturated aqueous ammonium chloride solution
4. dry with materialbrine and dried over anhydrous magnesium sulfate
5. filtrationThe mixture was filtered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel chromatoraphy
8. washeluting with hexanes-ethyl acetate (85:15)