Lithium hydroxide, monohydrate → HCID 10388029, compound

Participants

Reaction Steps

Lithium hydroxide monohydrate (0.020 g, 0.487 mmol) was added to a solution of 4-[4-benzo[1,3]dioxol-5-yl-5-(6-methyl-pyridin-2-yl)-1H-imidazol-2-yl]-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester (see Example 21; 0.150 g, 0.325 mmol) in a mixture of THF/MeOH/H2O (2/1/1, 4 mL). The mixture was stirred for 3 hours. Solvent was removed. Residue was diluted with water (30 mL). Citric acid was added to the solution to make the pH lower than 7. The aqueous solution was extracted with ethyl acetate. Ethyl acetate extract was washed with brine, dried over sodium sulfate, filtered and concentrated to give 0.140 g (99%) of the title compound as a yellow solid. MS (ESP+) m/z 432.2 (M+1). 1H NMR (400 MHz, Methanol-d4) δ 7.72 (m, 1H), 7.33 (d, 1H, J=7.7 Hz), 7.22 (d, 1H, J=7.7 Hz), 6.98 (m, 3H), 6.05 (s, 2H), 2.64 (s, 3H), 2.11 (m, 6H), 1.99 (m, 6H).

Provenance & Evidence