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Efficient and scalable synthesis of α,α-­disubstituted β-amino amides

Permanent link
https://hdl.handle.net/10037/9648
DOI
https://doi.org/10.1039/C6OB01219A
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Accepted manuscript version (PDF)
Date
2016-07-12
Type
Journal article
Tidsskriftartikkel
Peer reviewed

Author
Paulsen, Marianne Hagensen; Engqvist, Magnus; Ausbacher, Dominik; Strøm, Morten Bøhmer; Bayer, Annette
Abstract
A practical and efficient methodology for the preparation of 2-aminoethyl α,α-disubstituted β-amino amides in three steps from methyl cyanoacetate has been developed. The key step in the synthesis was the chemoselective reduction of the nitrile group in presence of an amide and aryl halide functionalities. Reduction with RANEY® Nickel catalyst, either with molecular hydrogen (8–10 bar) or under transfer hydrogenation conditions, necessitated in situ protection of the resulting amines with Boc2O, whereas aryl bromide containing nitriles could be chemoselectively reduced with ZnCl2/NaBH4 without debromination. The developed protocol involved only one chromatographic purification step and can be performed at gram scale.
Description
Accepted manuscript version. Publisher's version available at http://doi.org/10.1039/c6ob01219a.
Publisher
Royal Society of Chemistry
Citation
Organic and Biomolecular Chemistry 2016, 14, 7570
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