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

Participants

Reaction Steps

To a solution of the product from Step 5 (14.0 g, 21.5 mmol) in EtOH (300 mL) was added potassium vinyltrifluoroborate (5.05 g, 37.7 mmol), Et3N (5.25 mL, 37.7 mmol) and PdCl2(dppf)-DCM adduct (1025 mg, 1.26 mmol). The reaction mixture was then heated to reflux for 1.5 hours, cooled to RT, concentrated and partitioned between EtOAc and water. The layers were separated and the organic phase dried over Na2SO4, filtered and concentrated. The residue was purified on silica (gradient elution 10% to 80% EtOAc in hexanes) to give the title compound (10.4 g). LRMS (M+H)+ Calcd.: 505.2; found 505.5.

Provenance & Evidence