Water → tert-butyl (3R)-3-({5-[(1E)-3-methoxy-3-oxo-1-propen-1-yl]-2-pyrazinyl}amino)-1-pyrrolidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate (10.00 g), tert-butyl (3R)-3-amino-1-pyrrolidinecarboxylate (14.01 g) and potassium phosphate (21.30 g) in DMA (25 mL) was stirred at 90-95° C. for 6 hours under nitrogen atmosphere. After addition of water, the reaction mixture was extracted with AcOEt. Water was added to the organic layer and the mixture was adjusted to pH 8 with 1N HCl aq., washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give a residue. The residue was purified by silica gel (chromatorex NH) (hexane-AcOEt 60:40 v/v) to give tert-butyl (3R)-3-({5-[(1E)-3-methoxy-3-oxo-1-propen-1-yl]-2-pyrazinyl}amino)-1-pyrrolidinecarboxylate as a solid (10.64 g).

Provenance & Evidence