Ethyl propiolate → 3-Benzyl 2-tert-butyl (1R,3S,4S,6R)-6-{[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]oxy}-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate

Participants

Reaction Steps

To a solution of 3-benzyl 2-tert-butyl (1R,3S,4S,6R)-6-hydroxy-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate obtained in Example 30-1 (593 mg) in dichloromethane (10 mL), were added ethyl propiolate (670 mg) and 4-methylmorphorine (190 mg). The mixture was stirred at room temperature for 3 hrs. The resulting mixture was evaporated in vacuo and the residue was chromatographed on silica gel eluting with hexane and ethyl acetate (4:1) to give the target compound (760 mg).

Provenance & Evidence