Abstract
N-Methyl (V) and N-benzyl (VIII) derivatives of ethyl 2-(ethoxycarbonylmethylaminomethyl) isovalerate compound were obtained from ethyl 2-aminomethylisovalerate (II). (V) was obtained by N-methylation of (IV) with formaldehyde and (VIII) was obtained by condensation of (II) and benzaldehyde, reduction of its product, and further condensation with ethyl iodoacetate. These were submitted to the Dieckmann reaction using sodium hydride and the reaction afforded ethyl 1-methyl-4-isopropyl-3-pyrrolidone-2-carboxylate (IXa) and ethyl 1-benzyl-4-isopropyl-3-pyrrolidone-2-carboxylate (IXb). Hydrolysis of (IX) with dil. hydrochloric acid easily effected ketonic fission and 1-methyl-4-isopropyl-3-pyrrolidone (Xa) and 1-benzyl-4-isopropyl-3-pyrrolidone (Xb).
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