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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
An efficient synthesis of a spirocyclic oxindole analogue
Dawei Teng1, Hongxing Zhang, A Mendonca
1Department of Chemistry, ChemRoutes Corporation, Edmonton, Alberta T6E 5P8, Canada. tengdw@yahoo.com
Abstract:
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.
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