2-bromo-N-pyridin-2-yl-acetamide → (R)-1-(2-Oxo-2-(pyridin-2-ylamino)ethyl)-3-((1-phenylcycloheptane-1-carbonyl)oxy)quinuclidin-1-ium bromide

Participants

Reaction Steps

1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (0.79 mmol) and 2-bromo-N-pyridin-2-yl-acetamide (Example 15a) (0.87 mmol) were stirred together in anhydrous MeCN at room temperature for 2.5 days. The reaction mixture was concentrated in vacuo and the yellow solid purified by flash silica gel column chromatography eluting with 2-8% MeOH/dichloromethane to give a tan solid. The solid was dissolved up in refluxing MeCN and the solution was allowed to cool down to room temperature. The resulting crystals were filtered off and washed with a small quantity of cold MeCN to give the title compound (211 mg) as a white crystalline solid.

Provenance & Evidence