反应详情

In a dried reaction flask, (R)-tert-butyl pyrrolidin-3-ylcarbamate (5.774 g, 31.0 mmol) and formaldehyde solution (37%, 6.82 mL) were dissolved into methanol (124 mL) under a nitrogen protection. The mixture was stirred at room temperature for 1 hr. Sodium borohydride (3.518 g, 93.0 mmol) was added in portion under an ice bath. The mixture was stirred at room temperature for 3 hr. Water was added and the solution was concentrated under reduced pressure. Ethyl acetate and saturated aqueous sodium bicarbonate solution were added. The mixture was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered, purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:1) to produce a white solid (3.685 g) in 59.4% yield.

1. stirringThe mixture was stirred at room temperature for 3 hr
2. concentrationthe solution was concentrated under reduced pressure
3. additionEthyl acetate and saturated aqueous sodium bicarbonate solution were added
4. extractionThe mixture was extracted with ethyl acetate
5. washThe combined organic phase was washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. custompurified by silica gel column chromatography (ethyl acetate:petroleum ether=1:1)