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 → (1R,3S,4S,6R)-2-(tert-Butoxycarbonyl)-6-(3-ethoxy-3-oxopropoxy)-2-azabicyclo[2.2.1]heptane-3-carboxylic Acid

Participants

Reaction Steps

To a solution of 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 obtained in Example 30-2 (316 mg) in ethanol (8 mL), was added 10% palladium on carbon (60 mg). The mixture was stirred under 4 atm of hydrogen for 1 hr at room temperature. The resulting mixture was filtered through celite and washed with ethanol. The filtrate and washings were evaporated in vacuo and the residue was chromatographed on silica gel eluting with chloroform and methanol (19:1) to give the target compound (210 mg).

Provenance & Evidence