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

OTEVŘEL, Jan, David ŠVESTKA and Pavel BOBÁĽ. One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles. RSC Advances. Cambridge: Royal Society of Chemistry, 2020, vol. 10, No 42, p. 25029-25045. ISSN 2046-2069. Available from: https://dx.doi.org/10.1039/d0ra04359a.

Basic information

• Original name: One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles
• Authors: OTEVŘEL, Jan (203 Czech Republic, guarantor, belonging to the institution), David ŠVESTKA (203 Czech Republic, belonging to the institution) and Pavel BOBÁĽ (703 Slovakia, belonging to the institution).
• Edition: RSC Advances, Cambridge, Royal Society of Chemistry, 2020, 2046-2069.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 30104 Pharmacology and pharmacy
• Country of publisher: United Kingdom of Great Britain and Northern Ireland
• Confidentiality degree: is not subject to a state or trade secret
• WWW: Odkaz na plný text výsledku nebo domovskou stránku výsledku.
• Impact factor: Impact factor: 3.361
• RIV identification code: RIV/00216224:14160/20:00118227
• Organization unit: Faculty of Pharmacy
• Doi: http://dx.doi.org/10.1039/d0ra04359a
• UT WoS: 000545357500025
• Keywords in English: amides; cyanides; molecular oxygen
• Tags: CF PROT, rivok, ÚChL
• Tags: International impact, Reviewed

Abstract

We have identified a novel one-pot method for the synthesis of beta-amino alcohols, which is based on C-H bond hydroxylation at the benzylic alpha-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.

Links

• LM2015043, research and development project: Name: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)

Investor: Ministry of Education, Youth and Sports of the CR