3-(2-trimethylsilylethynyl)-1-azabicyclo[2.2.2]octan-3-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Dibromonitrophenol (3.0 g, 0.0119 mol), 3-[(trimethylsilyl)ethynyl]quinuclidin-3-ol (2.66 g, 0.0119 mol; obtained in Step 1), Cu2O (1.70 g, 0.0119 mol) and pyridine (200 mL) were added to a round bottom flask. The resulting mixture was heated at reflux overnight, filtered through Celite, and the solvent was evaporated. The residue was purified by chromatography on silica gel using ethyl acetate (250 mL) and methanol (500 mL) as eluents. The methanol fraction was evaporated to yield 1.12 g (29%) of the title compound. HPLC purity=90%, m/z=322 (M+H)+. The resulting mixture was heated at reflux overnight filtered through Celite the solvent was evaporated The residue was purified by chromatography on silica gel The methanol fraction was evaporated