Water → 1-t-Butyl 2-methyl (2S,4R)-4-[(7-methoxy-3-vinylquinolin-2-yl)oxy]pyrrolidine-1,2-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

TEA (0.87 mL, 6.23 mmol) was added to a solution of 1-tert-butyl 2-methyl (2S,4R)-4-[(3-bromo-7-methoxyquinolin-2-yl)oxy]pyrrolidine-1,2-dicarboxylate (2.0 g, 4.2 mmol) in EtOH (30 mL). Potassium vinyltrifluoroborate (0.84 g, 6.23 mmol) and PdCl2(dppf)-CH2Cl2 adduct (0.17 g, 0.21 mmol) were then added, and the reaction mixture was stirred at 100° C. for 2 h. The reaction mixture was worked up with EtOAc and water, and the layers were separated. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified on silica (gradient elution, 0-40% EtOAc/hexanes) to yield the title compound as an oil. LRMS (M+H-tBu)+=373.3.

Provenance & Evidence