Journal
SYNTHESIS-STUTTGART
Volume 55, Issue 3, Pages 499-509Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1915-7794
Keywords
morpholines; sulfamidates; stereoselectivity; chiral building blocks; privileged scaffolds
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In this study, a method for synthesizing optically pure morpholine building blocks from chiral pool material is reported, which is of great significance for improving the properties of active pharmaceutical ingredients.
Morpholine is a heterocyclic moiety that is widely used in medicinal chemistry as a building block. It has unique physicochemical properties, as it can improve both pharmacokinetic and pharmacodynamic properties of active pharmaceutical ingredients. However, the efficient synthesis of enantiomerically pure morpholine building blocks remains challenging. Herein, we report the synthesis of optically pure 3-hydroxymethylmorpholine building blocks, as well as their sulfamidates, exploiting a stereospecific strategy from chiral pool material.
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