Development of a Large-Scale Route to an MCH1 Receptor Antagonist: Investigation of a Staudinger Ketene–Imine Cycloaddition in Batch and Flow Mode

A practical large-scale route to an MCH1 receptor antagonist is described. A Staudinger β-lactam synthesis of an imine and an in situ generated ketene was utilized as a key step for the preparation of a spiro-azetidine building block. The reaction was demonstrated in both batch and flow mode and a c...

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Bibliographic Details
Published in:Organic process research & development 2015-12, Vol.19 (12), p.2067-2074
Main Authors: Karlsson, Staffan, Bergman, Rolf, Löfberg, Christian, Moore, Peter R, Pontén, Fritiof, Tholander, Joakim, Sörensen, Henrik
Format: Article
Language:English
Online Access:Get full text
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Summary:A practical large-scale route to an MCH1 receptor antagonist is described. A Staudinger β-lactam synthesis of an imine and an in situ generated ketene was utilized as a key step for the preparation of a spiro-azetidine building block. The reaction was demonstrated in both batch and flow mode and a comparison of these techniques is described.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.5b00319