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Synthesis of a cis 2,5-Disubstituted Morpholine by De-epimerization: Application to the Multigram Scale Synthesis of a Mineralocorticoid Antagonist

โœ Scribed by Sammons, Matthew; Jennings, Sandra M.; Herr, Michael; Hulford, Catherine A.; Wei, Liuqing; Hallissey, James F.; Kiser, E. Jason; Wright, Stephen W.; Piotrowski, David W.


Book ID
120351254
Publisher
American Chemical Society
Year
2013
Tongue
English
Weight
486 KB
Volume
17
Category
Article
ISSN
1083-6160

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โœ Cameron J Cowden; Robert D Wilson*; Brian C Bishop; Ian F Cottrell; Antony J Dav ๐Ÿ“‚ Article ๐Ÿ“… 2000 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 82 KB

Chlorotriazolinone 4 has been synthesised in a single step via the novel condensation of semicarbazide hydrochloride with orthoester 8. Alkylation of secondary amine 3 with compound 4 proceeds in 99% yield to afford the target NK 1 antagonist 1.