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

Participants

Reaction Steps

A 4 M HCl dioxane (38 mL) solution was added to a methanol (60 mL) solution of (R)-3-[N-(tert-butoxycarbonyl)glycyl]amino-1-(4-chlorobenzyl)pyrrolidine (5.39 g, 14.7 mmol). The resulting solution was stirred at room temperature for 2 hours. The reaction mixture was concentrated, and a 2 M solution (80 mL) of NaOH was added. The mixture solution was extracted with dichloromethane (80 mL×3), and the extracts were combined, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (SiO2, ethyl acetate/ethanol/triethylamine=90:5:5) to afford (R)-3-(glycylamino)-1-(4-chlorobenzyl)pyrrolidine (3.374 g, 86%) 1H NMR (CDCl3, 270 MHz) δ 1.77 (dd, J=1.3 and 6.9 Hz, 1H), 2.20-3.39 (m, 2H), 2.53 (dd, J=3.3 and 9.6 Hz, 1H), 2.62 (dd, J=6.6 and 9.6 Hz, 1H), 2.78-2.87 (m, 1H), 3.31 (s, 2H), 3.57 (s, 2H), 4.38-4.53 (br, 1H), 7.18-7.32 (m, 4H), 7.39 (br, s, 1H).

Provenance & Evidence