4-Nitrobenzoic Acid → (4-Nitrophenyl)(pyrrolidin-1-yl)methanone

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Reaction Steps

To a solution of 1.98 g of para-nitrobenzoic acid in 50 mL of dichloromethane are successively added under argon, at 0° C., 0.781 mL of pyrrolidine, 0.13 g of hydroxybenzotriazole, 2.3 g of 1,3-dimethylaminopropyl-3-ethyl carbodiimide and 3.43 mL of diisopropylamine. The reaction mixture is then stirred at room temperature for 15 hours and then washed with water. The organic phase is then washed with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a mixture of ethyl acetate and cyclohexane (60/40 by volume) to give 1.9 g of (4-nitrophenyl)pyrrolidin-1-yl-methanone, the characteristics of which are as follows:

Provenance & Evidence