Ethyl Acetate → HCID 131728520, compound

Participants

Reaction Steps

Sodium triacetoxyborohydride (0.244 g, 1.15 mmol) was added to a solution of enantiomerically enriched-(trans)-ethyl-2-(4-amino-2,5-difluorophenyl)cyclopropanecarboxylate (III-1e) (0.110 g, 0.46 mmol) and 3-phenoxybenzaldehyde (0.091 g, 0.46 mmol) in 5 mL of dichloroethane. The mixture was stirred at room temperature for one hour. The reaction mixture was partitioned between chlroroform and water. The organic phase was washed with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate and the solvent evaporated. The residue was purified by chromatography on silica gel with hexane:ethyl acetate to give 0.127 g (65% yield) of the title compound as a colorless oil. 1HNMR (400 MHz, CDCl3) δ 7.32 (t, J=8.61Hz, 2H), 7.29 (t, J=7.69 Hz, 2H), 7.10 (t, J=7.14 Hz, 1H), 7.06 (d, J=7.69 Hz, 1H), 6.99 (d, J=7.51 Hz, 2H), 6.90 (dd, J=3.11, 8.06 Hz, 1H), 6.55 (dd, J=6.78, 12.09 Hz, 1H), 6.28 (dd, J=7.51, 11.72 Hz, H), 4.36 (br s, 1H), 4.29 (d, J=5.68 Hz, 2H), 4.15 (q, J=7.14 Hz, 2H), 2.50 (m, 1H), 7.79 (m, 1H), 1.53 (m, 1H), 1.27 (t, J=7.14 Hz, 3H), 1.22 (m, 1H).

Provenance & Evidence