Itaconic acid → 1-(2-(Dimethylamino)ethyl)-5-oxopyrrolidine-3-carboxylic acid

HRID 552195

Reaktionsgleichung

Reaktionsgleichung von HRID 552195
[C:1]([OH:9])(=[O:8])[C:2]([CH2:4][C:5](O)=[O:6])=[CH2:3].[CH3:10][N:11]([CH3:15])[CH2:12][CH2:13][NH2:14]>CO>[CH3:10][N:11]([CH3:15])[CH2:12][CH2:13][N:14]1[C:5](=[O:6])[CH2:4][CH:2]([C:1]([OH:9])=[O:8])[CH2:3]1

Komponenten

4

Edukt 2

HCID 811Itaconic acidHCID 66053N,N-Dimethylethylenediamine

Produkt 1

HCID 6545211-(2-(Dimethylamino)ethyl)-5-oxopyrrolidine-3-carboxylic acidAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of commercially available itaconic acid and N,N-dimethylethylenediamine was heated up to 160° C. for about 20-25 minutes. The mixture was allowed to cool to 100° C. and then diluted with MeOH to prevent solidification. The product was obtained in a 56% yield after crystallization from MeOH/EtOAc. 1H-NMR (300 MHz, D2O): δ 2.63 (dd, 1H), 2.80 (dd, 1H), 2.95 (s, 6H), 3.15-3.25 (m, 1H), 3.32-3.44 (m, 1H), 3.44-3.76 (m, 4H), 3.82-3.94 (m, 1H). Retention Time (LC, method: ammonium acetate standard): 0.13 min. MS (M+H+): 201.0.

Aufarbeitung

  1. temperatureto cool to 100° C.
  2. customThe product was obtained in a 56% yield
  3. customafter crystallization from MeOH/EtOAc
  4. custom0.13 min

Quellen und Nachweise

ORD-Eintrag
ord-a4c008ff012d4516ae558864d9ce8f91
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951801B2

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