Sodium Hydroxide → HCID 58728079, compound

Participants

Reaction Steps

A solution of ethyl 1-[(4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidin-1-yl)carbonyl]cyclobutane-carboxylate from example 14 (0.050 g, 0.086 mmol), 5 N NaOH (10 ml) and ethanol (4 ml) was stirred at 90° C. for 3 hrs. The reaction was evaporated to dryness and residue was suspend in water (10 ml) and neutralized with 1N HCl. The aqueous layer was extracted with ethyl acetate (3×10 ml). The organic layer was dried using magnesium sulfate and concentrated down to form a white oil (0.032 g, 67%). 1H NMR (300 MHz, CDCl3) δ 7.68 (d, 1H), 7.27 (m, 8H), 4.63 (m, 1H), 3.84 (m, 1H), 3.41 (m, 1H), 3.25-2.95 (m, 4H), 2.87 (m, 1H), 2.58 (s, 3H), 2.45-2.20 (m, 4H), 2.05 (m, 2H), 1.89 (m, 8H), 1.63 (m, 5H), 1.61 (s, 2H). HRMS C34H42N4O3 m/z 555.3335 (M+H)Cal.; 555.3320 (M+H)Obs..

Provenance & Evidence