1,4-Dioxane hydrochloride → (R)-1-(4-chlorobenzyl)-3-(glycylamino)pyrrolidine

Participants

Reaction Steps

A 4M HCl dioxane (38 mL) solution was added to the methanol (60 mL) solution of the (R)-3-{N-(tert-butoxycarbonyl)glycyl}amino-1-(4-chlorobenzyl)pyrrolidine (5.39 g, 14.7 mmol). The solution was stirred at room temperature for 2 hours. The reaction mixture was concentrated and then mixed with a 2M NaOH solution (80 mL). The mixture was extracted with dichloromethane (80 mL×3), and the extracts were combined, dried over anhydrous sodium sulfate, and then concentrated. The (R)-3-(glycylamino)-1-(4-chlorobenzyl)pyrrolidine (3.374 g, 86%) was obtained by column chromatography (SiO2, AcOEt/EtOH/Et3N=90/5/5).

Provenance & Evidence