(2E)-3-(4-{[(benzyloxy)carbonyl]amino}-2-fluorophenyl)prop-2-enyl diazoacetate → benzyl 3-fluoro-4-[(1S,5R,6R)-2-oxo-3-oxabicyclo[3.1.0]hex-6-yl]phenylcarbamate

Participants

Reaction Steps

A solution of (2E)-3-(4-{[(benzyloxy)carbonyl]amino}-2-fluorophenyl)prop-2-enyl diazoacetate (13.9 g, 37.5 mmol) in 1,2-dichloroethane (150 mL) was added dropwise over 14 h to a refluxing solution of bis-(N-t-butylsalicylaldiminato)copper(II) (0.82 g, 1.9 mmol, prepared as described by R. G. Charles, J. Org. Chem. 1957, 22, 677) in 1.5 L of toluene. After the addition was complete, the reaction mixture was heated another hour at reflux, then cooled, filtered and concentrated. The crude oil was purified by column chromatography (0-50% ethyl acetate-hexanes) to provide the (racemic) title compound as a yellow solid.

Provenance & Evidence