Stereoselective synthesis of spiropiperidines as BACE-1 aspartyl protease inhibitors via late stage N-arylation of a 1,8-diazaspiro[4.5]dec-3-en-2-one pharmacophore.
J Org Chem
; 78(6): 2661-9, 2013 Mar 15.
Article
em En
| MEDLINE
| ID: mdl-23438191
ABSTRACT
A stereoselective synthesis of spiropiperidine compounds, exemplified by compound 1, was developed, which was based upon the late stage N-arylation of a 1,8-diazaspiro[4.5]dec-3-en-2-one pharmacophore. Previously, compound 1 was prepared in low overall yield from piperidinone 2 via the Strecker reaction. A new route was developed, which employed the stereospecific Corey-Link reaction of an enantiomerically pure trichloromethylcarbinol to give a template compound amenable to late stage N-arylation.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Piperidinas
/
Compostos de Espiro
/
Compostos Aza
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Ácido Aspártico Endopeptidases
/
Metanol
Idioma:
En
Ano de publicação:
2013
Tipo de documento:
Article