Synthesis of 4-substituted 3,3-difluoropiperidines.
J Org Chem
; 75(3): 929-32, 2010 Feb 05.
Article
em En
| MEDLINE
| ID: mdl-20050617
ABSTRACT
Synthetic strategies toward 4-substituted 3,3-difluoropiperidines were evaluated. 4-Alkoxymethyl- and 4-aryloxymethyl-3,3-difluoropiperidines were synthesized via 1,4-addition of ethyl bromodifluoroacetate to 3-substituted acrylonitriles in the presence of copper powder, followed by borane reduction of the cyano substituent, lactamization, and reduction of the lactam. This method was applied to establish the synthesis of N-protected 3,3-difluoroisonipecotic acid, a fluorinated gamma-amino acid. 4-Benzyloxy-3,3-difluoropiperidine was prepared using an analogous methodology and was converted to N-protected 3,3-difluoro-4,4-dihydroxypiperidine, a compound with high potential as a building block in medicinal chemistry.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Piperidinas
/
Hidrocarbonetos Fluorados
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2010
Tipo de documento:
Article
País de afiliação:
Bélgica