反应详情

温度

2.5 °C

To a solution of (S)-2-(dibenzylamino)pentanal (125 g; 0.444 mol) in methanol (375 mL) at 0-5° C. was added a previously cooled (0-5° C.) aqueous solution of sodium bisulfite (69.39 g, 0.667 mol; 150 mole %) in water (530 mL). The reaction mixture was stirred at 0-5° C. for 14 hours. A solution of sodium cyanide (32.02 g; 0.667 mol; 150 mol %) in water (402 mL), followed by ethyl acetate (1.25 L) was added to the above reaction mixture at 0° C. Stirring was continued at ambient temperature for 5 hours, monitoring progress of the reaction by TLC analysis (ethyl acetate/hexane, 1:9). Once the reaction was complete, the ethyl acetate layer was separated, washed with water (2×750 mL) and dried over sodium sulfate. The organic extract was concentrated under reduced pressure, washed with hexanes (200 mL), to provide 94 g of crude product as an off-white solid.

1. additionwas added to the above reaction mixture at 0° C
2. stirringStirring
3. waitwas continued at ambient temperature for 5 hours
4. customthe ethyl acetate layer was separated
5. washwashed with water (2×750 mL)
6. dry with materialdried over sodium sulfate
7. extractionThe organic extract
8. concentrationwas concentrated under reduced pressure
9. washwashed with hexanes (200 mL)