Trifluoroacetic acid → HCID 10958749, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diethyl acetamidomalonate (Aldrich, 1.25 g, 5.7 mmol) in ethanol (10 mL) under nitrogen was added freshly cut sodium metal (0.03 g, 1.4 mmol). The reaction mixture was stirred at room temperature until all sodium has dissolved. The reaction mixture was cooled to −40° C. (dry ice/acetonitrile) and a solution of 4-azidocyclopent-2-enone (0.7 g, 5.7 mmol) in ethanol (5 mL) was added dropwise over a period of 10 min. The reaction mixture was stirred at −40° C. for 30 min and quenched with trifluoroacetic acid (0.1 mL, 1.4 mmol). The solvent was removed in vacuo to furnish a white solid. Purification of the crude by flash column chromatography (60% ether in hexane) gave 1.2 g (63%) of trans-3-azido-4-[(methylcarbonyl-amino)bis(ethoxycarbonyl)methyl]cyclopentanone as a white solid, mp 121-122° C.

Provenance & Evidence