4-Nitrophenyl quinuclidin-3-yl carbonate → Quinuclidin-3-yl (1-(5-bromothiophen-3-yl)cyclopropyl)carbamate

Participants

Reaction Steps

To a stirred solution of 2-(5-bromothiophen-3-yl)propan-2-amine (0.366 g, 1.66 mmol) in THF (10 mL) was added 4-nitrophenyl quinuclidin-3-yl carbonate (0.571 g, 1.95 mmol) and a few granules of 4-(dimethylamino)pyridine. The mixture was refluxed overnight, concentrated and partitioned between ethyl acetate (50 mL) and aqueous NaHCO3 (50 mL). The organic layer was washed again with aqueous NaHCO3 (1×50 mL), dried (Na2SO4) and concentrated. The resulting dirty yellow gum was purified by flash chromatography using a chloloform/methanol/ammonia gradient to afford quinuclidin-3-yl(1-(5-bromothiophen-3-yl)cyclopropyl)carbamate as an off-white solid (0.305 g, 49%).

Provenance & Evidence