Development of a Practical Synthesis of Stearoyl-CoA Desaturase (SCD1) Inhibitor MK-8245
Organic Process Research & Development2011Vol. 15(5), pp. 1073–1080
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Mélina Girardin, Sarah J. Dolman, Sophie Lauzon, Stéphane G. Ouellet, G. Hughes, Paul Fernandez, George Zhou, Paul O’Shea
Abstract
A practical kilogram scale chromatography-free synthesis of stearoyl-CoA desaturase 1 (SCD1) inhibitor MK-8245 is described. The key features of this sequence include an efficient addition–elimination reaction of a piperidine fragment with a 3-bromoisoxaline followed by an iodine-mediated oxidation to the corresponding isoxazole. The development of a safe and scalable tetrazole formation protocol is also presented.
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