Citric Acid → 5-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]-1-pentanol

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Reaction Steps

5-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]-pentanoic acid (0.30 g, 0.53 mmol) prepared in Example 128 was mixed with N-hydroxysuccinimide (64 mg, 0.56 mmol), N,N-dimethylformamide (5 ml) and WSC (113 mg, 0.59 mmol), followed by stirring overnight at room temperature. To the resulting mixture, tetrahydrofuran (5 ml) and sodium borohydride (61 mg, 1.6 mmol) were added and stirred at room temperature for 4 hours. The reaction mixture was poured into 10% citric acid, extracted with ethyl acetate, washed with saturated brine, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was applied to silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/10) to give the titled compound (0.17 g, yield: 59%) as a white crystal (cis:trans=4:1).

Provenance & Evidence