Tetrahydrofuran → HCID 21714059, compound

Participants

Reaction Steps

4-Allyl-2-t-butyloxycarbonylamino-3-oxo-5-phenyl-3,4-dihydropyrazine (850 mg, 2.60 mmol) was dissolved in tetrahydrofuran (10.4 ml), and 4-methylmorpholine N-oxide (1.22 ml, 5.19 mmol) and 4% aqueous osmium tetroxide (0.83 mol. 0.13 mmol) was added to it, and the mixture was stirred overnight at room temperature. The reaction solution was diluted with ethyl acetate and then washed successively with saturated aqueous sodium thiosulfate, distilled water and saturated saline. The organic layer was dried over anhydrous magnesium sulfate, and the drying agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform/methanol=50/1) whereby title compound (750 mg, 80% yield) was obtained.

Provenance & Evidence