[Cl:1][C:2]1[C:11]([C:12]([O:14]C)=[O:13])=[C:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[C:4](=[O:16])[C:3]=1[F:17].[OH-].[Na+].Cl>C1COCC1.CO>[Cl:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[C:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[C:4](=[O:16])[C:3]=1[F:17]
Methyl 8-chloro-7-fluoro-6-oxo-2,3,4,6-tetrahydro-1H-quinolizine-9-carboxylate (7c, 600 mg, 2.43 mmol) was dissolved in THF (10 ml) and MeOH (5 ml). 1N NaOH (5 ml) was added and the solution stirred at RT overnight. The solution was acidified with 4N HCl then extracted into DCM and the aqueous washed ×3 with DCM. The organic portions were evaporated to give the title compound which was used without further purification (426 mg, 72%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.61-1.79 (m, 4H) 2.83 (t, J=6.06 Hz, 2H) 3.94 (t, J=6.32 Hz, 2H) 13.75 (br. s., 1H) [M+H] calc'd for C10H9ClFNO3, 246. found, 246.
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