4-Aminobenzoic Acid → 2-Azabicyclo(2.2.2)octan-3-one

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Reaction Steps

Suspend 5% rhodium/carbon (2 g) in water (50 mL) and add 4-aminobenzoic acid (27.4 g, 200 mmol) and dilute to 200 mL with water. Shake the mixture at 50 psi for 4 days, filter through glass fiber and evaporate the solvent in vacuo to a white solid. Mix the solid with diphenyl ether and heat quickly to reflux for 20 minutes. Cool and partition between hexane and water. Separate the organic phase and wash with water. Combine the aqueous phases, treat with sodium hydrogen carbonate and subject to continuous extraction with methylene chloride overnight. Evaporate the methylene chloride extracts in vacuo to give 3-isoquinuclidone as a white solid.

Provenance & Evidence