Ammonium Chloride → HCID 60004308, compound

Participants

Reaction Steps

A solution of tert-butyl (4R)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (14.0 g) in THF (250 mL) was cooled in a dry ice/acetone bath under nitrogen atmosphere, and ethyl magnesium bromide (24 mL, 3M solution in diethyl ether) was added dropwise thereto. The resulting mixture was stirred for 3 hr while elevating the temperature gradually to 0° C., and saturated aqueous ammonium chloride solution was added thereto. The mixture was separated into phases, the aqueous layer was then extracted with ethyl acetate, and the organic layer was washed with water and brine. After drying over anhydrous magnesium sulfate, the desiccant was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=92:8-37:63) to afford tert-butyl (4R)-4-(1-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (11.14 g).

Provenance & Evidence