Water → 9-[8-(2,2,2-Trifluoro-acetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthene-3-carbonitrile

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Reaction Steps

To a solution of Compound 5d (3 g, 6.46 mmol) in DMF (100 mL) was added CuCN (0.69 g, 7.70 mmol). The reaction mixture was refluxed for 2 d and then cooled to room temperature. The mixture was poured into water (100 mL), and extracted with EtOAc (3×100 mL). The combined organic layers were washed sequentially with H2O (100 mL), brine (100 mL), then dried (MgSO4) and concentrated. The crude product was purified by normal phase chromatography, using a gradient of ethyl acetate (0% to 10%) in heptane to give compound 5e. MS m/z (M+H+) 410.9; 1H NMR (CDCl3) δ 1.41 (m, 2H), 1.85 (m, 2H), 2.96 (m, 4H), 4.44 (m, 1H), 4.73 (m, 1H), 7.23 (m, 3H), 7.33 (m, 2H), 7.43 (dt, 1H), 7.51 (m, 1H).

Provenance & Evidence