Issue 42, 2020

One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles

Abstract

We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C–H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target.

Graphical abstract: One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles

Supplementary files

Article information

Article type
Paper
Submitted
15 maj 2020
Accepted
09 jun 2020
First published
30 jun 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 25029-25045

One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles

J. Otevrel, D. Svestka and P. Bobal, RSC Adv., 2020, 10, 25029 DOI: 10.1039/D0RA04359A

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