Ethanolamine → N-(2-hydroxyethyl)-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide

HRID 620859

Reaktionsgleichung

Reaktionsgleichung von HRID 620859
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH:4]([C:14]([O:16]C)=O)[CH2:3]1.[NH2:18][CH2:19][CH2:20][OH:21]>CO>[OH:21][CH2:20][CH2:19][NH:18][C:14]([CH:4]1[CH2:3][C:2](=[O:1])[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:5]1)=[O:16]

Komponenten

4

Edukt 2

HCID 700EthanolamineHCID 98909Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylate

Produkt 1

HCID 14280883N-(2-hydroxyethyl)-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamideAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 46.7 g (0.2 mole) of methyl 5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxylate [J. Org. Chem., 26, 1519 (1961)], 36.7 g (0.6 mole) of 2-aminoethanol and 500 ml methanol was refluxed overnight. The reaction was cooled to room temperature and the solvent removed at reduced pressure. The residue was taken up in dichloromethane and extracted 3×100 ml 1N sodium hydroxide. The aqueous layer was taken to pH 5, extracted 3×150 ml dichloromethane, then taken to pH 8 and again extracted 3×150 ml dichloromethane. The aqueous layer was concentrated at reduced pressure and the resulting slurry stirred in dichloromethane. The salts were filtered off. The combined organic layers were dried over magnesium sulfate, the solvent removed at reduced pressure to Yield 47.9 g of N-(2-hydroxyethyl)-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide as an oil. This was used in the next step without further purification.

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. customthe solvent removed at reduced pressure
  3. extractionextracted 3×100 ml 1N sodium hydroxide
  4. extractionextracted 3×150 ml dichloromethane
  5. extractionagain extracted 3×150 ml dichloromethane
  6. concentrationThe aqueous layer was concentrated at reduced pressure
  7. filtrationThe salts were filtered off
  8. dry with materialThe combined organic layers were dried over magnesium sulfate
  9. customthe solvent removed at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8cffe67242db4981bc44b2bad854cb4e
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04822801

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