A convergent approach to the synthesis of aprepitant: a potent human NK-1 receptor antagonist

A convergent approach to enantiomerically pure aprepitant a potent orally active antagonist of the human neurokinin-1 (NK-1) receptor, is described. A simple and convergent approach to enantiomerically pure 5-[[2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy-3-(4-fluorophenyl)morpholin-4-yl]methyl]-1,2-...

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Bibliographic Details
Published in:	Tetrahedron letters Vol. 48; no. 45; pp. 8001 - 8004
Main Authors:	Elati, Chandrashekar R., Kolla, Naveenkumar, Gangula, Srinivas, Naredla, Anitha, Vankawala, Pravinchandra J., Avinigiri, Muttu L., Chalamala, Subrahmanyeswararao, Sundaram, Venkatraman, Mathad, Vijayavitthal T., Bhattacharya, Apurba, Bandichhor, Rakeshwar
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 05-11-2007
Online Access:	Get full text
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Summary:	A convergent approach to enantiomerically pure aprepitant a potent orally active antagonist of the human neurokinin-1 (NK-1) receptor, is described. A simple and convergent approach to enantiomerically pure 5-[[2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy-3-(4-fluorophenyl)morpholin-4-yl]methyl]-1,2-dihydro-1,2,4-triazol-3-one 1, a potent orally active antagonist of the human neurokinin-1 (NK-1) receptor, is described. The synthetic procedure starts from p-fluorobenzaldehyde to access the racemic morpholinone 2 via a modified Strecker synthesis and utilizes a diastereomeric salt resolution technique to accomplish the synthesis of 1 in enantiomerically pure form and good yield.
Bibliography:	ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 23
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2007.09.051