Ethyl Acetate → HCID 68772483, compound

Participants

Reaction Steps

Sodium triacetoxyborohydride (0.297 g, 1.40 mmol) was added to a solution of enantiomerically enriched-(cis)-ethyl-2-(4-aminophenyl)cyclopropanecarboxylate (0.115 g, 0.56 mmol) (III-1c) and 4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde (0.152 g, 0.56 mmol) in 5 mL of dichloroethane. The mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and the solvent evaporated. The residue was purified by chromatography on silica gel with hexane:ethyl acetate to give 0.186 g (72% yield) of (cis)-ethyl-2-{4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxylate (III-2e) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.96 (d, J=8.06 Hz, 2H), 7.63 (d, J=8.24 Hz, 2H), 7.10 (d, J=8.24 Hz, 2H), 6.57 (d, J=8.61 Hz, 2H), 4.43 (s, 2H), 3.91 (br s, 1H), 3.87 (q, J=7.14 Hz, 2H), 2.48 (s, 3H), 2.48 (m, 1H), 2.00 (m, 1H), 1.63 (m, 1H), 1.27 (m, 1H), 1.00 (t, J=7.14 Hz, 3H).

Provenance & Evidence