Acetic Acid → Diethyl 3,3-dimethylpyrrolidine-2,2-dicarboxylate

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Reaction Steps

Diethyl benzyloxycarbonylaminomalonate (3.09 g, 10 mM) was dissolved in dry ethanol (15 ml) and added to a solution of sodium ethoxide (from 100 mg sodium) in ethanol (3 ml). 3-Methylbut-2-enal (840 mg, 10 mM) in ethanol (6 ml) was added and the solution stirred at 25° for 24 hrs. Acetic acid (0.28 ml) was then added and the solution hydrogenated for 24 hrs using palladium on carbon (10% 500 mg) as catalyst. The solution was filtered, evaporated and the residue chromatographed on silica column using ether/petroleum ether (40°-60°) (1 : 1) as eluant to give 2,2-dicarboethoxy-3,3-dimethylpyrrolidine (0.9 g).

Provenance & Evidence