Salicylaldehyde → 3-Hydroxy-3-{1-[(2-hydroxybenzylidene)amino]ethyl}pyrrolidine-1-carboxylic acid benzyl ester

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A solution of 3-(1-aminoethyl)-3-hydroxypyrrolidine-1-carboxylic acid benzyl ester (Example A10, 0.34 g, 0.93 mmol) and salicylaldehyde (0.147 g, 1.2 mmol) in dry ethanol (5 mL) is refluxed for 3 hours. After evaporation of the solvent, the residue is purified by column chromatography (30:70:0.01 ethyl acetate/hexanes/ammonium hydroxide) to afford the title compound (0.12 g). 1H NMR (200 MHz, CDCl3): δ 8.39 (s, 1H), 7.41–7.25 (m, 7H), 6.97–6.85 (m, 2H), 5.09 (s, 2H), 3.65–3.34 (m, 5H), 2.01–1.87 (m, 2H), 1.37–1.32 (m, 3H).

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