Synthesis of a cis 2,5-Disubstituted Morpholine by De-epimerization: Application to the Multigram Scale Synthesis of a Mineralocorticoid Antagonist
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- 作者：Matthew Sammons ; Sandra M. Jennings ; Michael Herr ; Catherine A. Hulford ; Liuqing Wei ; James F. Hallissey ; E. Jason Kiser ; Stephen W. Wright ; David W. Piotrowski
- 刊名：Organic Process Research & Development
- 出版年：2013
- 出版时间：June 21, 2013
- 年：2013
- 卷：17
- 期：6
- 页码：934-939
- 全文大小：302K
- 年卷期：v.17,no.6(June 21, 2013)
- ISSN：1520-586X
文摘
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.