(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate → HCID 11265628, compound

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Reaction Steps

A solution of t-butyl N-{(1S)-2-[methoxy(methyl)amino]-1-methyl-2-oxoethyl}carbamate (50 g) in tetrahydrofuran (700 mL) was gradually added dropwise at 0° C. to a 2.5M 4-fluorophenylmagnesium bromide/tetrahydrofuran solution (300 mL) which had been prepared previously. The mixture was stirred at room temperature for 14 hours, cooled to 0° C., and extracted twice with ether after addition of saturated aqueous sodium bicarbonate. The organic layer was washed successively with saturated aqueous sodium bicarbonate and saturated brine, and dried over anhydrous sodium sulfate. After removal of the sodium sulfate by filtration, the organic solvent was evaporated off in vacuo. The resulting residue was purified by column chromatography on silica gel (C-300; hexane:ethyl acetate=4:1) to give the title compound.

Provenance & Evidence