(S,E)-tert-butyl 4-(4-(5,6-dichloro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)styryl)-2,2-dimethyloxazolidine-3-carboxylate → (S)-tert-butyl 4-(4-(5,6-dichloro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)phenethyl)-2,2-dimethyloxazolidine-3-carboxylate

Participants

Reaction Steps

To a stirred suspension of (S,E)-tert-butyl 4-(4-(5,6-dichloro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)styryl)-2,2-dimethyloxazolidine-3-carboxylate (220 mg) in methanol (8 ml) was added 10% platinum on charcoal (42 mg) and the mixture was then stirred under an atmosphere of hydrogen at room temperature for 2 hours. The mixture was then filtered through celite and the filtrate was concentrated in vacuo to afford (S)-tert-butyl 4-(4-(5,6-dichloro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)phenethyl)-2,2-dimethyloxazolidine-3-carboxylate (166 mg, 75%) as a white amorphous solid. MS (ISP): 538.3 ([{37Cl35Cl}M+NH4]+), 536.2 ([{35Cl}M+NH4]+), 521.3 ([{37Cl35Cl}M+H]+), 519.2 ([{35Cl}M+H]+), 465.3 ([{37Cl35Cl}M+H—C4H8]+), 463.1 ([{35Cl}M+H—C4H8]+).

Provenance & Evidence