(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one → (R)-Methyl 3-[2-[[2-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-[(tert-butyldimethylsilyl)oxy]ethyl]amino]-2-methylpropyl]benzoate

Participants

Reaction Conditions

Reaction Steps

Methyl 3-(2-amino-2-methylpropyl)benzoate (1 g, 4.82 mmol) was added to (R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one (1.57 g, 3.22 mmol) neat. The resulting mixture was heated to 95° C. for 3 d then cooled. Chromatography (1:3, hexanes/EtOAc) afforded the title compound (970 mg, 49%) as light yellow oil. ES/MS calcd. for C36H47N2O5Si+ 615.3. Found m/z=615.3 (M+H)+.

Provenance & Evidence