Hydrochloric Acid → Methyl (4R)-4-[(7-methoxy-2-phenyl-6-vinylquinolin-4-yl)oxy]-L-prolinate hydrochloride

Participants

Reaction Conditions

Reaction Steps

Tributylvinylstannane (1.15 eq.) and tetrakis(triphenylphosphine) palladium(0) (0.07 eq.) were added to a solution of compound 116 in toluene (0.09 M) and the reaction mixture was heated at 100° C. After 20 h volatiles were removed in vacuo and the residue was purified by column chromatography (SiO2, PE:EtOAc with EtOAc from 1 to 60%) to give a pale yellow solid, that was taken up in a 4N solution of HCl in dioxane (0.31 M). The reaction mixture was stirred for 1 h and the resulting white solid recovered by filtration, washed with EtOAc/petroleum ether affording the title compound 117 (99%) as a pale yellow solid. MS (ES+) m/z 405 (M+H)+.

Provenance & Evidence