Stereoselective preparation of a cyclopentane-based NK1 receptor antagonist bearing an unsymmetrically substituted sec-sec ether.
J Org Chem
; 71(19): 7378-90, 2006 Sep 15.
Article
em En
| MEDLINE
| ID: mdl-16958533
ABSTRACT
A highly efficient synthesis of the potent and selective NK-1 receptor antagonist 1 is described. The key transformation involved the etherification reaction between cyclopentanol 12 and chiral imidate 30 which was catalyzed by HBF4 to initially give ether 14 as a 171 mixture of diastereomers and in 75% combined yield. The diastereoselectivity was upgraded to 1091 by crystallization of the triethylamine solvate 44 which was isolated in 54% yield from 12. Mechanistic studies confirmed that the etherification reaction proceeds through an unprecedented S(N)2 reaction pathway under typical S(N)1 reaction conditions.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Ciclopentanos
/
Antagonistas dos Receptores de Neurocinina-1
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2006
Tipo de documento:
Article