Regioselective, electrochem. synthesis of heterocyclic α-amino amides

Publikationstyp:
Patent
Metadaten:
Abstract
The present invention relates to regioselective chem. and electrochem. processes for the preparation of an oxidized heterocyclic alpha-amino amide compounds I wherein Z is bound to the heterocyclic ring via single or double bond and either OH or O; n is 0 or an integer between 1 and 4; R1 and R3 independently of each other represent H or a straight chain or branched, saturated or non-saturated hydrocarbon group having 1 to 6 carbon atoms; R3 and R4 independently of each other represent H, a straight-chain or branched, saturated or non-saturated hydrocarbon group having 1 to 6 carbon atoms or form, together with the nitrogen atom to which they are bound, a saturated or non-saturated, non-aromatic or aromatic, heterocyclic 4- to 7-membered ring group carrying one or more ring heteroatoms. By applying specific catalysts or catalyst systems during chem. oxidation or by applying particular electrochem. oxidation conditions the present invention provides access to valuable alpha amino amide compounds, which are oxidized at the heterocyclic amino group by regioselective introduction of either a hydroxyl or a keto group. In a more particular embodiment, the present invention describes a chem. oxidation reaction, which advantageously is applicable in the enantioselective synthesis of valuable oxidized heterocyclic alpha-amino amide compounds, like levetiracetam, brivaracetam or the synthesis of piracetam. Another aspect of the present invention relates to a process for the electrochem. recycling of alkali perhalogenate oxidants as spent during said regioselective oxidation reactions of the invention. Still another aspect of the invention relates to the electrochem. preparation of perhalogenates.
Autoren
  • SR Waldvogel
  • S Arndt
  • D Weis
  • K Donsbach
  • AM Nauth
  • T Opatz
Schlüsselwörter
  • heterocyclic amino amide regioselective electrochem synthesis
Notes
CAplus AN 2021:2339324 (Patent)
Datum der Datenerfassung
2024
Awarded date
2021
Titel
Regioselective, electrochem. synthesis of heterocyclic α-amino amides

Datenquelle: Manual

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