Water → Racemic-(trans)-2-[4-({[5-(4-chlorophenyl)-2-furanyl]methyl}amino)phenyl]cyclopropanecarboxylic acid

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To a mixture of (of racemic-(trans)-2-(4-aminophenyl)cyclopropanecarboxylic acid (I-1) (0.057 g, 0.322 mmol) in dichloroethane (2.5 mL) was added 5-(2-chlorophenyl)furfural (0.059 g, 0.285 mmol). The mixture was stirred for 2 days followed by addition of sodium triacetoxyborohydride (0.097 g, 0.458 mmol). The mixture was stirred for 7 h at RT. Water was added (10 mL), and the layers were separated. The aqueous phase was extracted with CH2Cl2 (2×10 mL). The combined organics were dried with MgSO4 and concentrated. The crude material was purified by chromatography (EtOAc/hexanes) to give the title compound as a yellow solid (0.06 g, 60%). 1H NMR (400 MHz, DMSO-d6): δ 12.13 (s, 1H), 7.64 (d, J=8.6 Hz, 2H), 7.43 (d, J=8.6 Hz, 2H), 6.87 (d, J=3.3 Hz, 1H), 6.85 (d, J=8.4 Hz, 2H), 6.57 (d, J=8.4 Hz, 2H), 6.36 (d, J=3.3 Hz, 1H), 6.03 (t, J=6.0 Hz, 1H), 4.25 (d, J=6.0 Hz, 2H), 2.19 (m, 1H), 1.58 (m, 1H), 1.28 (m, 1H), 1.17 (m, 1H). ES-MS m/z 366.13 (MH−).

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