1436416-04-4Relevant articles and documents
Synthesis of a cis 2,5-disubstituted morpholine by de-epimerization: Application to the multigram scale synthesis of a mineralocorticoid antagonist
Sammons, Matthew,Jennings, Sandra M.,Herr, Michael,Hulford, Catherine A.,Wei, Liuqing,Hallissey, James F.,Kiser, E. Jason,Wright, Stephen W.,Piotrowski, David W.
, p. 934 - 939 (2013/07/26)
A convergent route to multigram quantities of a mineralocorticoid antagonist 3 is described. Starting from (R)-phenylglycinol, the synthesis of cis 2,5-morpholine 2 is accomplished utilizing a de-epimerization to install the second stereogenic center. The multigram synthesis of 3 was completed through a sequence of an SNAr reaction, Dakin oxidation, alkylation, and cyclization to provide a crystalline solid.