1-Chloroethyl chloroformate → 3-(3,5-Dichlorophenyl)-3-(trifluoromethyl)pyrrolidine

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Reaction Steps

The solution of 1-benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (5.7 g) and 1-chloroethyl chloroformate (4.4 g) in dichloroethane was heated to reflux for 3 hours. The mixture was cooled to room temperature and then concentrated under the reduced pressure. Methanol was added to the resultant residue, which was then heated with stirring at 60° C. for two hours. The mixture was cooled to room temperature, to which was then added water. The solution was washed twice with the mixed solvent of hexane and ethyl acetate (9:1). The solution was alkalized with sodium hydrogen carbonate and then extracted with ethyl acetate three times. The organic layer was combined, which was then washed with brine and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was distilled away under the reduced pressure to yield 3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (4.2 g). 1H-NMR (CDCl3) δ: 2.24-2.33 (1H, m), 2.51-2.56 (1H, m), 2.97-3.07 (1H, m), 3.19-3.26 (2H, m), 3.74 (1H, d), 7.25 (2H, d), 7.35 (1H, t)

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