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

HRID 2372058Notes

Reaction equation

HRID 2372058 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 14280883N-(2-hydroxyethyl)-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamideYield 91.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e6ca604a416c47e7a36c7543b008d88a
Source dataset
uspto-grants-1992_03
Patent number
US05097032

Reaction notes

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