Telescoped Lithiation, C-Arylation and Methoxylation in Flow-Batch Hybrid toward the Synthesis of Canagliflozin

    • Dominik Polterauera,b
    • Jason D. Williamsa,b
    • Christopher A.Honea,b
    • C. Oliver Kappea,b
    • aCenter for Continuous Flow Synthesis and Processing (CCFLOW), Research Center Pharmaceutical Engineering (RCPE), Inffeldgasse 13, A-8010 Graz, Austria
    • bInstitute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, A-8010 Graz, Austria

    We report a highly efficient three-step flow-batch hybrid procedure for the synthesis of a key canagliflozin intermediate. The telescoped process provides exquisite control over an exothermic and mixing sensitive lithiation and subsequent C-arylation within a microstructured flow reactor. Methoxylation reagents are then added in flow, before undergoing completion in a batch vessel. The flow process afforded the target intermediate in 76% yield, with a throughput of 26.8 g/h.

    Read the publication that featured this abstract

    Get in touch

    For more information on flow chemistry systems and services please use the contact methods below.

    Call us on +44 (0)1284 728659 or Email us