(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one → (R)-8-(benzyloxy)-5-(1-((tert-butyldimethylsilyl)oxy)-2-(methylamino)ethyl)quinolin-2(1H)-one

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Reaction Steps

A solution of (R)-8-(benzyloxy)-5-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)quinolin-2(1H)-one (1.5 g, 3.1 mmol) in methylamine/tetrahydrofuran (2.0 M, 16 mL, 32 mmol) was heated in a sealed tube at 100° C. (oil bath) for 3 days. After allowing the mixture to cool to room temperature, it was concentrated and purified via automated flash silica gel chromatography, using a 25 g Silicycle SiliSep flash column (dichloromethane/methanol/ammonium hydroxide). Concentration of the desired fractions under reduced pressure provided the title compound. ES/MS calcd. for C25H35N2O3Si+ 439.2. Found m/z=439.3 (M+H)+.

Provenance & Evidence