Synthesis of Tris[2‐(dimethylamino)ethyl]amine with Regiospecific Deuterium Labels - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue ChemistrySelect Année : 2023

Synthesis of Tris[2‐(dimethylamino)ethyl]amine with Regiospecific Deuterium Labels

Résumé

Simple synthetic routes to regioselectively deuterated tris[2-(dimethylamino)ethyl]amine (Me6TREN) variants are described. Imine formation with formaldehyde-d2 from tris(2-aminoethyl)amine (TREN) and subsequent reductions with NaBD4 afforded N[CH2CH2N(CD3)2]3 or d18-Me6TREN in 79 % yield. A trisubstitution protocol from 2-bromo-N,N-dimethylacetamide and ammonium carbonate and subsequent reduction of the N(CH2CONMe2)3 intermediate by lithium aluminum deuteride has afforded N[CH2CD2N(CH3)2]3 or (d6-arm)-Me6TREN in three steps and 52 % overall yield. A similar protocol from 2-bromo-N,N-dimethyl-d2-acetamide, obtained in two steps from d4-acetic acid, with reduction of the N(CD2CONMe2)3 intermediate by lithium aluminum hydride has afforded N[CD2CH2N(CH3)2]3 or (d6-cap)-Me6TREN in four steps and 13 % overall yield from CD3COOD.
Fichier principal
Vignette du fichier
Sobieski, Synthesis of Tris[2-(dimethylamino)ethyl, 2023.pdf (587.29 Ko) Télécharger le fichier
10.1002-slct.202300053-Original Data.zip (3.3 Mo) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)

Dates et versions

hal-03971862 , version 1 (03-02-2023)

Identifiants

Citer

Julian Sobieski, Illia Ruzhylo, Grzegorz Szczepaniak, Adam Gorczyński, Krzysztof Matyjaszewski, et al.. Synthesis of Tris[2‐(dimethylamino)ethyl]amine with Regiospecific Deuterium Labels. ChemistrySelect, 2023, 8 (5), pp.e202300053. ⟨10.1002/slct.202300053⟩. ⟨hal-03971862⟩
51 Consultations
72 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More