Cesium carbonate → 2-Phenyl-2-aza-bicyclo[2.2.2]octan-3-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-azabicyclo[2.2.2]octan-3-one (0.6 g, 4.8 mmol), iodo benzene (1.16 g, 5.76 mmol), Cs2CO3 (2.36 g, 7.20 mmol), xantphos (0.22 g, 0.38 mmol) and 1,4-dioxane (30 ml) was charged in a sealed tube and degassed with argon gas for 15 min. Tetrakis(triphenylphosphine)palladium (0) (0.22 g, 0.19 mmol) was added and degassed for another 15 min and heated at 125° C. for 3 h. The reaction mixture was filtered and concentrated under reduced pressure to afford the crude compound. This was purified by column chromatography over neutral alumina using 0.5% MeOH in CHCl3 as eluent to afford 600 mg (62%) of 2-phenyl-2-aza-bicyclo[2.2.2]octan-3-one as pale yellow solid.

Provenance & Evidence