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The safe use of diazo reagents for the preparation of a key structure in the synthesis of milnacipran analogues is described herein. Using continuous flow technology, the diazo reagent is synthesized, purified, dried, and subsequently used in semi-batch mode for an intramolecular cyclopropanation. Side products formed in the reaction are isolated and rationalized to optimize the process. Different separation techniques in flow are compared with regard to their ability to produce pure and dry diazo reagents. The studies yield a scalable process to a key intermediate in the syntheses of milnacipran and its possible substituted analogues.

Toward a Large-Scale Approach to Milnacipran Analogues Using Diazo Compounds in Flow Chemistry

Simon T. R. Müller^†, Aurélien Murat^‡, Paul Hellier^§, and Thomas Wirth^*^†

^† School of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, U.K.

^‡ Institut de Recherche Pierre Fabre, 81603 Gaillac, France

^§ Pierre Fabre Médicament, Parc Industriel de la Chartreuse, 81106 Castres, France

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.5b00308

Publication Date (Web): October 29, 2015

*E-mail: wirth@cf.ac.uk.

http://pubs.acs.org/doi/abs/10.1021/acs.oprd.5b00308

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An immobilised monolithic iridium hydrogen transfer catalyst has been developed for use in flow based processing. The monolithic construc thas been used for several redox reductions demonstrating excellent recyclability, good turnover numbersand high chemical stability giving negligible metal leaching over extended periods of use.

A FlowSyn Auto-LF system was employed to automatically process a library of 40 aldehydes and ketones.

Maria Victoria Rojo,*a Lucie Guetzoyana and Ian. R. Baxendale Org. Biomol. Chem., 2015, 13, 1768

An immobilised iridium hydrogen transfer catalyst has been developed for use in flow based processing by incorporation of a ligand into a porous polymeric monolithic flow reactor. The monolithic construct has been used for several redox reductions demonstrating excellent recyclability, good turnover numbers and high chemical stability giving negligible metal leaching over extended periods of use.