Ammonium Chloride → 3-[3-(4-methoxyphenylamino)butyryl]-1,3-oxazolidin-2-one

Participants

Reaction Steps

In a stream of nitrogen, a solution of 3-crotonoyl-1,3-oxazolidin-2-one (78 mg, 0.5 mmol), anisidine trifluoromethanesulfonate (205 mg, 0.75 mmol) and Pd((R)-binap)(μ-OH)]2(OTf)2 (4.6 mg, 0.0025 mmol) in tetrahydrofuran (0.5 mL) was stirred at room temperatures for 12 hours. When no starting material remained was observed, a saturated aqueous solution of ammonium chloride was added to quench the reaction, and the resulting mixture was extracted with ethyl acetate. The organic layer was concentrated and purified by a silica gel column chromatography (hexane:ethyl acetate=1:1) to give the objective 3-[3-(4-methoxyphenylamino)butyryl]-1,3-oxazolidin-2-one (128 mg, 92% yield). The enantiomeric excess ratio was determined to be 98% e.e. by a liquid chromatography with an optical isomer separating column (column: AD-H).

Provenance & Evidence