Hydrochloric Acid → (2R,5S)-1-Benzyl-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-2-carboxylic acid ethyl ester

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Reaction Steps

To a suspension of (2R,5S)-1-benzyl-pyrrolidine-2,5-dicarboxylic acid monoethyl ester (2 g, 7.21 mmol) in DMF (25 mL) was added 3-(trifluoromethoxy)aniline (1.53 mL, 8.65 mmol), HBTU (4.19 g, 10.8 mmol) and diisopropylethylamine (3.78 mL, 21.6 mmol). The reaction mixture was stirred at RT overnight. EtOAc and 1N HCl were added, the layers were separated and the aqueous one was back-extracted with EtOAc (×3). The combined organic extracts were washed with an aqueous solution containing 5% of NaHCO3, dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc gradient 100:0 to 80:20) to give the title compound. MS (LC/MS): 437.2 [M+H]+; tR (HPLC conditions b) 5.50 min.

Provenance & Evidence