[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][C:3]1=2.N1[CH2:20][CH2:19][CH2:18][CH2:17]1.O.C(O[CH2:26][CH3:27])(=O)C>CO>[CH:26]1([CH:27]=[C:11]2[CH2:10][CH2:9][C:8]3[N:7]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][C:3]=3[C:2]2=[O:1])[CH2:20][CH2:19][CH2:18][CH2:17]1In a dried reaction flask, methyl 5-oxo-5,6,7,8-tetrahydroquinoline-2-carboxylate (1.97 g, 9.6 mmol), cyclopentylcarbaldehyde (2.05 mL, 19.20 mmol), and pyrrolidine (1.6 mL, 19.39 mmol) were dissolved in methanol (19 mL) at room temperature. In the protection from light and under the nitrogen atmosphere, the mixture was stirred at room temperature for 6 hr. To the mixture were added water and ethyl acetate. The mixture was extracted with ethyl acetate. The combined organic phase was washed with saturated salt water, dried over anhydrous sodium sulfate and purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:10) to obtain a pale yellow solid (1.589 g) in 58.0% yield.
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