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

HRID 464970

반응식

HRID 464970 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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) 2-aminoethanol and 500 ml methanol were 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 with 3×100 ml 1N sodium hydroxide. The aqueous layer was taken to pH 5 with hydrochloric acid, extracted with 3×150 ml dichloromethane, then taken to pH 8 with sodium hydroxide solution 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.

후처리

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

출처 및 근거

ORD 기록
ord-7c6a7bf4b89f4360999b6378f4125607
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04550103

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