反应详情

1-Benzyl-4-hydroxy-3-azidomethylpyrrolidine (59.7 g) is added to chloroform (100 ml), and the mixture is saturated with dry hydrogen chloride gas. A solution of thionyl chloride (61.2 g) in chloroform (100 ml) is added dropwise to the mixture under reflux. After refluxing for 2 hours, the mixture is concentrated. To the residue is added ethanol and the excess thionyl chloride is removed, and then, the mixture is again concentrated. After neutralizing the concentrate with an aqueous sodium hydrogen carbonate, the mixture is extracted with dichloromethane. The dichloromethane layer is washed with water, dried and concentrated, and the resulting residue is then purified by silica gel column chromatography (solvent, ethyl acetate-n-hexane) to give 1-benzyl-3-azidomethyl-4-chloropyrrolidine (26.0 g) as an yellow oil.

1. temperatureunder reflux
2. temperatureAfter refluxing for 2 hours
3. concentrationthe mixture is concentrated
4. additionTo the residue is added ethanol
5. customthe excess thionyl chloride is removed
6. concentrationthe mixture is again concentrated
7. concentrationconcentrate with an aqueous sodium hydrogen carbonate
8. extractionthe mixture is extracted with dichloromethane
9. washThe dichloromethane layer is washed with water
10. customdried
11. concentrationconcentrated
12. customthe resulting residue is then purified by silica gel column chromatography (solvent, ethyl acetate-n-hexane)