1-Chloro-4-(chloromethyl)benzene → (R)-tert-Butyl (1-(4-chlorobenzyl)pyrrolidin-3-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

4-Chlorobenzyl chloride (4.15 g, 25.8 mmol) and iPr2NEt (6.67 g, 51.6 mmol) were added to a DMF (50 mL) solution of 3-[(tert-butoxycarbonyl)amino]pyrrolidine (4.81 g, 25.8 mmol). The reaction mixture was stirred at 70° C. for 15 hours, and the solvent was removed under reduced pressure. The objective 3-[(tert-butoxycarbonyl)amino]-1-(4-chlorobenzyl)pyrrolidine (6.43 g, 80%) was obtained as an off-white solid by recrystallization (acetonitrile, 50 mL). 1H NMR (CDCl3, 300 MHz) δ 1.37 (s, 9H), 1.5-1.7 (br, 1H), 2.1-2.4 (m, 2H), 2.5-2.7 (m, 2H), 2.83 (br, 1H), 3.57 (s, 2H), 4.1-4.3 (br, 1H), 4.9-5.1 (br, 1H), 7.15-7.35 (br, 4H); the purity was determined by RPLC/MS (98%). ESI/MS m/e 311.0 (M++H, C16H24ClN2O2).

Provenance & Evidence