Lithium hydroxide, monohydrate → (R)-Quinuclidin-3-yl((3-(3-hydroxypropoxy)phenyl)(phenyl)methyl)carbamate

Participants

Reaction Steps

To a stirred solution of 3-(3-(phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)-methyl)phenoxy)propyl benzoate (0.370 g, 0.72 mmol) in methanol (3.6 mL), was added a solution of lithium hydroxide monohydrate (0.060 g, 1.44 mmol) in water (1.2 mL). The reaction mixture was stirred at room temperature for 1 hour. Further lithium hydroxide monohydrate (0.060 g, 1.44 mmol) was added, and the reaction stirred at room temperature for a further 16 hours. The reaction mixture was heated at 40° C. for 3.5 hours and allowed to cool. The solvent was evaporate at reduced pressure, and the residue partitioned between ethyl acetate and water. The aqueous phase was further extracted with ethyl acetate (×2). The combined organic extracts were washed with 10% aqueous potassium carbonate (×2), saturated brine, and dried with anhydrous sodium sulfate. The mixture was filtered and the solvent evaporated at reduced pressure to afford the title compound (0.275 g, 93%).

Provenance & Evidence