Water → HCID 87568173, compound

Participants

Reaction Steps

To a mixture of racemic-(trans)-2-(4-aminophenyl)cyclopropanecarboxylic acid (I-1) (0.071 g, 0.401 mmol) in dichloroethane (3 mL) was added 5-[4-(trifluoromethyl)phenyl]-2-furancarbaldehyde (0.081 0.337 mmol). The mixture was stirred for 12 h followed by addition of sodium triacetoxyborohydride (0.110 g, 0.519 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 (0.051 g, 17%). 1H NMR (400 MHz, DMSO-d6): δ 7.83 (d, J=8.2 Hz, 2H), 7.74 (d, J=8.4 Hz, 2H), 7.06 (d, J=3.5 Hz, 1H), 6.87 (d, J=8.4 Hz, 2H), 6.59 (d, J=8.4 Hz, 2H), 6.42 (d, J=3.3 Hz, 1H), 4.29 (s, 2H), 2.20 (m, 1H), 1.59 (m, 1H), 1.29 (m, 1H), 1.19 (m, 1H). ES-MS m/z 400.02 (MH−).

Provenance & Evidence