Hydrochloric Acid → 2-(2-(3,4-Diethoxybenzyloxy)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetic Acid

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-(2-(3,4-diethoxybenzyloxy)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate (0.100 g, 0.221 mmol) in 1,4-dioxane (4 mL) was added 1.0 M LiOH (aq) (1.107 mL, 1.107 mmol). The reaction was stirred at 23° C. for 16 h in a 20 mL sealed scintillation vial. The mixture was poured into 1 M HCl and extracted with EtOAc (3×5 mL). The organic layers were combined, dried over MgSO4, and filtered by vacuum filtration through a glass fiber paper. The solvent was removed under reduced pressure to give the title compound (0.0831 g) as a tan solid. LCMS m/z=424.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.27-1.36 (m, 6H), 1.49 (d, J=11.37 Hz, 1H), 1.87-1.95 (m, 1H), 1.99-2.07 (m, 1H), 2.07-2.16 (m, 1H), 2.40-2.49 (m, 1H), 2.77-2.87 (m, 1H), 3.24-3.35 (m, 1H), 3.73-3.84 (m, 1H), 3.96-4.06 (m, 4H), 4.07-4.16 (m, 1H), 4.96 (s, 2H), 6.14 (s, 1H), 6.76 (dd, J=8.78, 2.34 Hz, 1H), 6.88-6.96 (m, 2H), 7.01-7.07 (m, 2H), 7.21 (d, J=8.84 Hz, 1H), 12.27 (s, 1H).

Provenance & Evidence