Hydrochloric Acid → HCID 13959885, compound

Participants

Reaction Steps

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.

Provenance & Evidence