1,4-Dioxane hydrochloride → (R)-1-(4-chlorobenzyl)-3-(glycylamino)pyrrolidine
Reaction equation
O1CCOCC1.Cl.C(OC([NH:15][CH2:16][C:17]([NH:19][C@@H:20]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH2:21]1)=[O:18])=O)(C)(C)C>CO>[NH2:15][CH2:16][C:17]([NH:19][C@@H:20]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=2)[CH2:21]1)=[O:18]Participants
4
Procedure
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).