Water → (trans)-Ethyl-2-{4-[({3-[(3,4-dichlorophenyl)oxy]phenyl}methyl)amino]phenyl}-cyclopropanecarboxylate

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To a mixture of (+)-(trans)-ethyl-2-(4-aminophenyl)cyclopropanecarboxylate (III-1b) (0.099 g, 0.482 mmol) in dichloroethane (3.0 mL) was added 3-(3,4-dichlorophenoxy)benzaldehyde (0.116 g, 0.434 mmol). The mixture was stirred for 12 h followed by addition of sodium triacetoxyborohydride (0.140 g, 0.660 mmol). The mixture was stirred for 6 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 (0.17 g, 85%, mixture of ethyl and methyl ester). 1H NMR (400 MHz, CDCl3) δ 7.35-7.31 (m, 2H), 7.14 (d, J=7.5 Hz, 1H), 7.05-7.00 (m, 2H), 6.92-6.87 (m, 3H), 6.81 (dd, J=8.8 Hz, 2.7 Hz, 1H), 6.52 (d, J=8.4 Hz, 2H), 4.31 (s, 2H), 4.14 (q, J=7.1 Hz, 2H), 2.42 (m, 1H), 1.77 (m, 1H), 1.51 (m, 1H), 1.28-1.20 (t+m, 4H).

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