Water → Racemic-(trans)-2-{4-[({5-[4-(trifluoromethyl)phenyl]-2-thienyl}methyl)amino]phenyl}cyclopropanecarboxylic acid trifluoroacetate

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To a mixture of racemic-(trans)-2-(4-aminophenyl)cyclopropanecarboxylic acid (I-1) (0.058 g, 0.327 mmol) in dichloroethane (2.5 mL) was added 5-[4-(trifluoromethyl)phenyl]-2-thiophenecarbaldehyde (0.071 0.277 mmol). The mixture was stirred for 12 h followed by addition of sodium triacetoxyborohydride (0.090 g, 0.425 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 EtOAc (3×10 mL). The combined organics were dried with MgSO4 and concentrated. The crude material was purified by preparative HPLC (10% to 100% CH3CN/H2O with 0.05% TFA) to give the title compound as a yellow solid (0.048 g, 15%). 1H NMR (400 MHz, DMSO-d8): δ7.77 (d, J=8.2 Hz, 2H), 7.69 (d, J=8.4 Hz, 2H), 7.51 (d, J=3.7 Hz, 1H), 7.06 (d, J=3.7 Hz, 1H), 6.85 (d, J=8.4 Hz, 2H), 6.55 (d, J=8.6 Hz, 2H), 4.43 (s, 2H), 2.19 (m, 1H), 1.59 (m, 1H), 1.28 (m, 1H), 1.18 (m, 1H). ES-MS m/z 416.03 (MH−).

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