Tributylvinyltin → 1-tert-butyl 2-methyl (2S,4R)-4-[(2-phenyl-6-vinylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-tert-butyl 2-methyl (2S,4R)-4-[(6-bromo-2-phenylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate 24 (1.45 g, 2.75 mmol) in toluene (20 mL) was added vinyltributyltin (0.96 mL, 3.3 mmol) and tetrakis-triphenylphosphine palladium (318 mg, 0.27 mmol). The mixture was then heated to 110° C. for 3 h, at which time, LC-MS revealed the disappearance of starting material. The reaction mixture was concentrated and purified on silica gel (gradient elution 15% to 50% EtOAc in hexanes) to give 1-tert-butyl 2-methyl (2S,4R)-4-[(2-phenyl-6-vinylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate 25 (0.74 g, 56% yield) as a yellow solid. LRMS (M+H)+ Calcd.: 475. found 475.

Provenance & Evidence