Potassium vinyltrifluoroborate → 1-t-Butyl 2-methyl (2S,4R)-4-[(7-methoxy-2-phenyl-6-vinylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate

Participants

Reaction Steps

Potassium vinyltrifluoroborate (5.05 g, 37.7 mmol), TEA (5.25 mL, 37.7 mmol) and PdCl2(dppf)-CH2Cl2 adduct (1025 mg, 1.26 mmol) were added to a solution of the product from step 5 (14.0 g, 21.5 mmol) in EtOH (300 mL). The mixture was then heated to reflux for 1.5 h, at which time LC-MS revealed the disappearance of starting material. The reaction mixture was cooled and concentrated and partitioned between EtOAc and water. The layers were separated, and the organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel (gradient elution 10% to 80% EtOAc in hexanes) to give the title compound (10.4 g, 82% yield). LRMS (M+H)+ Calcd.: 505.2; found 505.5.

Provenance & Evidence