Lithium hydroxide, monohydrate → HCID 86672698, compound

Participants

Reaction Steps

A mixture of (R)-methyl 1-(3-(quinuclidin-3-ylamino)propyl)-1H-indole-7-carboxylate (317 mg, 0.93 mmol) from Step C above and lithium hydroxide monohydrate (117 mg, 2.8 mmol) in tetrahydrofuran/water (1:1, 20 mL) was stirred at reflux until the reaction was complete by LC-MS. The solvent was removed under reduced pressure to give lithium (R)-1-(3-(quinuclidin-3-ylamino)propyl)-1H-indole-7-carboxylate as an off-white solid (574 mg, quantitative yield): 1H NMR (500 MHz, CD3OD) δ 7.49 (d, J=7.5 Hz, 1H), 7.26 (d, J=7.0 Hz, 1H), 7.19 (d, J=3.0 Hz, 1H), 6.98 (t, J=7.5 Hz, 1H), 6.43 (d, J=3.0 Hz, 1H), 4.51 (d, J=7.0 Hz, 2H), 3.05-2.99 (m, 1H), 2.83-2.68 (m, 5H), 2.49-2.32 (m, 3H), 2.01-1.92 (m, 2H), 1.71-1.61 (m, 3H), 1.51-1.47 (m, 1H), 1.36-1.28 (m, 1H); MS (ESI+) m/z 328 (M+H).

Provenance & Evidence