4‑Methyltetrahydropyran as a Convenient Alternative Solvent for Olefin Metathesis Reaction: Model Studies and Medicinal Chemistry Applications
journal contributionposted on 2020-11-25, 19:07 authored by Tomasz Nienałtowski, Paweł Krzesiński, Marcel E. Baumert, Aleksandra Skoczeń, Ewa Suska-Kauf, Jolanta Pawłowska, Anna Kajetanowicz, Karol Grela
A number of metathesis reactions were successfully conducted in 4-methyltetrahydropyran, including both standard model dienes, as well as more complex substrates, such as analogues of biologically active compounds and active pharmaceutical ingredients. To place this solvent in a context of pharmaceutical R + D, larger-scale syntheses of SUAM 1221, a prolyl endopeptidase inhibitor with potential application in Alzheimer disease treatment, and a derivative of sildenafil, an analogue of the popular Viagra drug, were executed. In the latter case, despite all the setup being made in air, the metathesis reaction at a 33 g scale proceeded very well with relatively low catalyst loading and without need of aqueous workup or column chromatography.
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Model Studieslatter caseSUAMOlefin Metathesis ReactionConvenientMethyltetrahydropyranAlzheimer disease treatmentanaloguemetathesis reactionSolventapplicationprolyl endopeptidase inhibitorcatalyst loadingingredientworkupmetathesis reactionsViagra drugcompoundmodel dienes4- methyltetrahydropyransubstrate33 g scalesildenafilsetupcolumn chromatographylarger-scale synthesesMedicinal Chemistry Applicationscontext