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Molecules 2006, 11(9), 700-706; doi:10.3390/11090700

An Efficient Synthesis of a Spirocyclic Oxindole Analogue

* ,  and
Department of Chemistry, ChemRoutes Corporation, Edmonton, Alberta T6E 5P8, Canada
* Author to whom correspondence should be addressed.
Received: 13 August 2006 / Revised: 6 September 2006 / Accepted: 14 September 2006 / Published: 14 September 2006
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An efficient, scaleable synthesis approach towards the spirocyclic oxindole analogue 1’-(tert-butoxycarbonyl)-2-oxospiro[indoline-3,4’-piperidine]-5-carboxylic acid (1) is described. The key steps are dianion alkylation and cyclization of ethyl 2- oxindoline-5-carboxylate (4) and demethylation of the resulting spirocyclic oxindole ethyl 1’-methyl-2-oxospiro[indoline-3,4’-piperidine]-5-carboxylate (5). The target compound was obtained in an overall yield of 35 % over eight steps without resorting to chromatographic purification.
Keywords: Spirocyclic oxindole; dianion alkylation; N-demethylation. Spirocyclic oxindole; dianion alkylation; N-demethylation.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Teng, D.; Zhang, H.; Mendonca, A. An Efficient Synthesis of a Spirocyclic Oxindole Analogue. Molecules 2006, 11, 700-706.

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