Lithium Hydroxide → (7-Fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetic acid

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Reaction Steps

To a solution of 5-ethoxycarbonylmethylene-7-fluoro-1-oxo-1,3,4,5-tetrahydro-azepino[3,4-b]indole-2,10-dicarboxylic acid di-tert-butyl ester, (1.31 g, 2.6 mmol) in MeOH—H2O (3:1 mixture, 150 mL) is added LiOH (0.312 g, 13 mmol). The mixture is stirred at room temperature for 2 days and concentrated. Water (100 mL) is added to the residue and it is acidified with 2M NaHSO4. The precipitate is collected by filtration and dried to give (7-fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetic acid; 1H NMR (DMSO-d6) δ 2.26 (d, 2H, J=5.2 Hz), 2.79 (s, 2H), 5.00 (t, 1H, 6.4 Hz), 6.22 (dt, 1H, J1=2.4 Hz, J2=10.8 Hz), 6.56 (dd, 1H, J1=4.0 Hz, J2=8.8 Hz), 6.66 (dd, 1H, J1=2.4 Hz, J2=10.8 Hz), 7.26 (t, 1H, J=5.6 Hz), 11.10 (s, 1H); m/z [M++1] 275.0.

Provenance & Evidence