Targeting a mirabegron precursor by BH3-mediated continuous flow reduction process

• Sonia De Angelis^a
• Claudia Carlucci^a
• Modesto de Candia^a
• Gabriele Rebuzzini^b
• Paolo Celestini^b
• Massimiliano Riscazzi^b
• Renzo Luisi^a
• Leonardo Degennaro^a

• ^a FLAME-Lab − Flow Chemistry and Microreactor Technology Laboratory, Department of Pharmacy — Drug Sciences, University of Bari “A. Moro” Via E. Orabona 4, Bari 70125, Italy
• ^b COSMA S.p.A, Via Colleoni 15/17, Ciserano, BG 24040, Italy

A continuous-flow reduction of (R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylacetamide, involved in the synthetic pathway of Mirabegron, has been developed. This study demonstrated the possibility to safely handling BH3 complexes within microfluidic reactors using 2-MeTHF as greener alternative to traditional solvents, and without requiring any additive such as DMI. In addition, NMR and HPLC purity analysis revealed that the sole by-product of this process is the diamine 3, which wouldn’t affect the following synthetic steps towards Mirabegron.

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