Triethylamine → Methyl (3S,4R)-4-(4-chlorophenyl)pyrrolidine-3-carboxylate hydrochloride

Participants

Reaction Steps

To a solution of methyl (3S,4R)-1-benzyl-4-(4-chlorophenyl)pyrrolidine-3-carboxylate, from preparation 25 (0.93 g, 2.8 mmol) in dichloromethane (9 mL) cooled with an ice-bath was added 1-chloroethyl chloroformate (0.46 mL). The reaction mixture was allowed to warm to room temperature and stirred for 48 hours. The reaction mixture was then cooled to 0° C. and triethylamine (0.43 mL, 3.1 mmol) was added followed by additional 1-chloroethylchloroformate (0.31 mL, 2.8 mmol). The ice-bath was removed and the reaction mixture was stirred at room temperature for 1.5 hours before being diluted with dichloromethane, washed with water (20 mL), 5% aqueous citric acid (20 mL) and then dried over magnesium sulfate and filtered. The solvent was removed in vacuo and the residual oil was refluxed in methanol (20 mL) for 1 hour. The solvent was then removed in vacuo and the residue was triturated with diethyl ether and filtered to give the desired product as a white solid, 0.874 g.

Provenance & Evidence