P-Anisidine → 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 (776 mg, 5.0 mmol), anisidine trifluoromethanesulfonate (1.64 g, 6.0 mmol), anisidine (3.1 mg, 0.005 mmol) and Pd((R)-segphos)(H2O)2(OTf)2 (26.3 mg, 0.005 mmol) in tetrahydrofuran (5 ml) was stirred at room temperatures for 24 hours. When no starting material remained was noticed, 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 (1.16 g, in a yield of 83%). The enantiomeric excess ratio was determined to be 97% e.e. by a liquid chromatography with an optical isomer separating column (column: AD-H).

Provenance & Evidence