(3R)-1-azabicyclo[2.2.2]octan-3-yl carbonochloridate hydrochloride → HCID 118114661, compound

Participants

Reaction Steps

To a stirred solution of methyl 5-((4-(amino(phenyl)methyl)phenoxy)methyl)-furan-2-carboxylate (301 mg, 0.894 mmol) in anhydrous pyridine (5 mL) at 0° C. under nitrogen was added (R)-quinuclidin-3-yl carbonochloridate hydrochloride (243 mg, 1.07 mmol, prepared as previously reported in 16, Step 6) in one portion. The reaction was stirred at room temperature for 3 days. The reaction was quenched by addition of 10% K2CO3 solution, extracted with ethyl acetate (3×20 mL). The combined organic phases were washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo. The residue was purified by silica gel chromatography, eluting with 0-10% 7N methanolic ammonia in ethyl acetate, to give the title compound as a yellow oil (280 mg, 64%).

Provenance & Evidence