Methanol → tert-Butyl [(3R)-5-oxo-1-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl}pyrrolidin-3-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

To a mixture of tert-butyl [(3R)-1-{4-[(benzyloxy)methyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl}-5-oxopyrrolidin-3-yl]carbamate (15.0 g, 32.1 mmol), ammonium formate (6.93 g, 110 mmol), methanol (250 ml) and tetrahydrofuran (93 ml) was added 10% Palladium on carbon (50% wet, 15.0 g) and the mixture was heated under reflux for 1 hour on an oil bath at 100° C. Ammonium formate (7.00 g, 111 mmol) was added and the mixture was further heated under reflux for 1 hour. Subsequently the catalyst was removed by filtration and the residue was washed thoroughly with a mixed solvent of chloroform-methanol (1:1). The filtrate and washings were combined to remove the solvent under reduced pressure and the residue was suspended in water from which the insoluble material was removed by filtration. The residue was washed with water and dried with heating under reduced pressure. 10.33 g (93%) of the title compound was obtained in the form of a white solid.

Provenance & Evidence