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A Simple and Expedient Procedure for the Preparation of Gabapentin Lactam (2-Aza-spiro[4,5]decan-3-one)

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journal contribution
posted on 12.09.2016, 00:00 by Jashuva V. P. Katuri, Vadiraj S. Ekkundi, Kuppuswamy Nagarajan
A novel process has been described on 100 g scale for the preparation of gabapentin lactam which is a penultimate intermediate for the preparation of gabapentin, comprising a Hofmann reaction of 1,1-cyclohexanediacetic acid monoamide using chlorinating agents such as trichloroisocyanuric acid, sodium dichloroisocyanurate, 1,3-dichloro-5,5-dimethylhydantoin, and N-chlorosuccinimide, which have not been employed so far for making this molecule. Reactions done in aqueous alkali on the 1,1-cyclohexanediacetic acid monoamide led to a solution of gabapentin sodium salt which on heating led to the formation of the gabapentin lactam in good yield.