3-Nitrophenylboronic Acid → HCID 57054725, compound

Participants

Reaction Steps

8-Methyl-3-trifluoromethylsulphonyloxy-8-azabicyclo[3.2.1]oct-2-ene (D9) (0.400 g, 1.48 mmol) was dissolved in DME (10 ml) and lithium chloride (0.188 g, 4.44 mmol) was added followed by 3-nitrobenzeneboronic acid (0.284 g, 1.70 mmol), and 2M sodium carbonate solution (4 ml). Argon was then bubbled through the mixture and after 5 minutes Pd(PPh3)4 (0.086 g, 0.074 mmol) was added. The mixture was then heated to reflux with stirring. After 4.5 h the reaction mixture was allowed to cool and was left at room temp. for 12 h, before being partitioned between chloroform and water. The aqueous layer was then extracted with chloroform (2×) and the combined organic layers were dried (Na2SO4) and evaporated under reduced pressure to give a brown oil that was dried in vacuo. The oil was purified by silica-gel chromatography (200:10.1, CH2Cl2MeOH:NH3 as eluant) to give the title compound as a brown oil (0.147 g, 46%).

Provenance & Evidence