Water → Ethyl 6,7,8-trifluoro-1,4-dihydro-1-[1-(2-hydroxyethyl)cyclopentyl]-4-oxo-3-quinolinecarboxylate

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Reaction Steps

To an iced solution of ethyl 3-[1-(2-hydroxyethyl)-cyclopentylamino]-2-(2,3,4,5-tetrafluorobenzoyl)acrylate (22.7 g, 56.3 mmol) in THF (200 mL) was added NaH (3.60 g, 90.0 mmol), and the mixture was stirred at room temperature for 1 hour. Water was added to the mixture portionwise at 0° C. The resulting mixture was extracted with ethyl acetate, and the combined organic extracts were concentrated in vacuo. Flash chromatography (AcOEt:Hexane=2:1) of the residue give the title compound as a colorless solid (14.1 g, 65%). 1H-NMR (400 MHz, DMSO-d6) δ 1.27 (3H, t, J=7.3 Hz), 1.53-1.75 (4H, m), 2.10-2.26 (4H, m), 2.31-2.44 (2H, m), 4.23 (2H, q, J=7.3 Hz), 4.55-4.60 (1H, m), 7.99-8.07 (1H, m), 8.80 (1H, s).

Provenance & Evidence