3,3-Dimethylbutanal → Neotame

Participants

Reaction Steps

Aspartame hydrochloride salt (10 mmol) and 3,3-dimethylbutyraldehyde (10 mmol) were dissolved in methanol (100 ml) in a hydrogenation vessel. Sodium hydrogen carbonate (NaHCO3, 12 mmol) and 5% palladium on carbon (100 mg) were added. The mixture was hydrogenated at 30-40 psi for 2 days at room temperature. After completion of the reaction, the catalyst was removed from the reaction mixture by filtration and washed with methanol (3×20 ml). The combined organic solvent was removed under reduced pressure below 40° C., and the residue was extracted using methylene chloride. The wet product was dried over sodium sulfate, and the solvent was removed in vacuo below 40° C. to give neotame in 90% yield.

Provenance & Evidence