methyl (E)-3-(4-chlorophenyl)prop-2-enoate

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of benzyl-methoxymethyl-trimethylsilanylmethyl-amine (2.05 mL, 8.0 mmol) and (E)-3-(4-chloro-phenyl)-acrylic acid methyl ester (1.57 g, 8.0 mmol) in dichloromethane (16 mL) was added TFA (275 mg, 2.4 mmol). The mixture was stirred at 23° C. for 30 min then treated with saturated aqueous NaHCO3 (20 mL), extracted with dichloromethane (2×50 mL), dried with MgSO4, filtered, and concentrated. Purification of the crude by flash chromatography (SiO2, hexane to 1:1 hexane:EtOAc) gave (trans)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester (2.11 g, 80%). extracted with dichloromethane (2×50 mL) dried with MgSO4 filtered concentrated Purification of the crude by flash chromatography (SiO2, hexane to 1:1 hexane:EtOAc)

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of benzyl-methoxymethyl-trimethylsilanylmethyl-amine (2.05 mL, 8.0 mmol) and (E)-3-(4-chloro-phenyl)-acrylic acid methyl ester (1.57 g, 8.0 mmol) in dichloromethane (16 mL) was added TFA (275 mg, 2.4 mmol). The mixture was stirred at 23° C. for 30 min then treated with saturated aqueous NaHCO3 (20 mL), extracted with dichloromethane (2×50 mL), dried with MgSO4, filtered, and concentrated. Purification of the crude by flash chromatography (SiO2, hexane to 1:1 hexane:EtOAc) gave (trans)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester (2.11 g, 80%). extracted with dichloromethane (2×50 mL) dried with MgSO4 filtered concentrated Purification of the crude by flash chromatography (SiO2, hexane to 1:1 hexane:EtOAc)