Direct Reductive Amination of Aldehyde Bisulfite Adducts Induced by 2‑Picoline Borane: Application to the Synthesis of a DPP-IV Inhibitor

Direct Reductive Amination of Aldehyde Bisulfite Adducts Induced by 2‑Picoline Borane: Application to the Synthesis of a DPP-IV Inhibitor

Aldehyde-bisulfite adducts dervied from unstable parent aldehydes were reductively alkylated in a direct fashion with a variety of amines. This approach features the use of 2-picoline borane as the reducing agent and a protic solvent for the reaction media and has been successfully applied to the sy...

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Veröffentlicht in:Journal of organic chemistry 2013-02, Vol.78 (4), p.1655-1659
Hauptverfasser: Faul, Margaret, Larsen, Rob, Levinson, Adam, Tedrow, Jason, Vounatsos, Filisaty
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
Alkylation
Amination
Amines - chemistry
Boranes - chemistry
Dipeptidyl Peptidase 4 - agonists
Dipeptidyl Peptidase 4 - chemistry
Morpholines - chemistry
Picolines - chemistry
Sulfites - chemistry
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Zusammenfassung:Aldehyde-bisulfite adducts dervied from unstable parent aldehydes were reductively alkylated in a direct fashion with a variety of amines. This approach features the use of 2-picoline borane as the reducing agent and a protic solvent for the reaction media and has been successfully applied to the synthesis of a DPP-IV inhibitor and a variety of other amines.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo3023878