N,N'-Dimethylethylenediamine → {(3R)-1-[4-(Methoxymethyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-5-oxopyrrolidin-3-yl}carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of [(3R)-5-oxopyrrolidin-3-yl]carbamic acid tert-butyl ester (synthesized with reference to WO2004/22536; 200 mg, 0.999 mmol), 6-bromo-4-(methoxymethyl)-2H-1,4-benzoxazin-3(4H)-one (272 mg, 0.999 mmol), potassium carbonate (415 mg, 3.0 mmol), copper (I) iodide (190 mg, 0.999 mmol), N,N′-dimethylethylenediamine (0.107 ml, 0.999 mmol) and toluene (4 ml) was stirred overnight at 100° C. under a stream of nitrogen gas. After cooling, dichloromethane was added to the reaction solution and insoluble material was removed by filtration. The solvent of the filtrate was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 375 mg (96%) of the title compound in the form of a colorless foamy solid.

Provenance & Evidence