Large-Scale Continuous Flow Transformation of Oximes into Fused-Bicyclic Isoxazolidines: An Example of Process Intensification

Here, we report a continuous flow protocol for the [3 + 2] cycloaddition of nitrones, in situ generated from oximes, into bicyclic isoxazolidines. This thermal process required very high temperatures to be efficient that were not easily reached in conventional reactors. A couple of examples are pres...

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Bibliographic Details
Published inOrganic process research & development Vol. 19; no. 2; pp. 347 - 351
Main Authors Rincón, Juan A, Mateos, Carlos, García-Losada, Pablo, Mergott, Dustin J
Format Journal Article
LanguageEnglish
Published American Chemical Society 20.02.2015
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Summary:Here, we report a continuous flow protocol for the [3 + 2] cycloaddition of nitrones, in situ generated from oximes, into bicyclic isoxazolidines. This thermal process required very high temperatures to be efficient that were not easily reached in conventional reactors. A couple of examples are presented and in both the flow process showed a greater performance than the batch mode. The process intensification study allowed the generation of 120 g/h of a key pharmaceutical intermediate.
ISSN:1083-6160
1520-586X
DOI:10.1021/op500350y