Selectfluor → (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-4-fluoro-1-oxo-1,2-dihydroisoquinolin-3-yl)ethylcarbamate

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Reaction Steps

A mixture of (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-1-oxo-1,2-dihydroisoquinolin-3-yl)ethylcarbamate 79 (2.75 g, 6.1 mmol, 1.0 eq) and selectfluor (2.16 g, 6.1 mmol, 1.0 eq) in anhydrous acetonitrile (100 mL) was stirred at reflux under argon for 12 h. The mixture was allowed to cool to RT and then concentrated in vacuo. The residue was dissolved in ethyl acetate (100 mL) and filtered through celite. The filtrate was washed with water, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (10-50% ethyl acetate-hexanes) to afford the product (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-4-fluoro-1-oxo-1,2-dihydroisoquinolin-3-yl)ethylcarbamate 80.

Provenance & Evidence