Isopropylamine → 5-oxo-1-(phenylmethyl)-N-(2-propyl)3-pyrrolidinecarboxamide

HRID 464994노트

반응식

HRID 464994 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]([OH:16])=O)[CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:29]([NH2:32])([CH3:31])[CH3:30]>C(#N)C>[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:5][CH:4]([C:14]([NH:32][CH:29]([CH3:31])[CH3:30])=[O:16])[CH2:3]1

참가 물질

5

반응물 3

HCID 6363IsopropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 990241-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid

생성물 1

HCID 47935185-oxo-1-(phenylmethyl)-N-(2-propyl)3-pyrrolidinecarboxamide수율 95.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

To a solution of 16.4 g (75.0 mmole) of 5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxylic acid in 150 ml of acetonitrile was added 13.8 g (85.0 mmole) of 1,1'-carbonyldiimidazole. The reaction was heated to 60° C. for one hour, cooled to room temperature and treated with 5.0 g (85 mmole) of isopropylamine. The reaction was stirred at room temperature for 18 hours, the solvent removed in vacuo and the residue partitioned between chloroform and water. The organic layer was washed with water, 1N hydrochloric acid, dried over magnesium sulfate and evaporated in vacuo to give 18.6 g to give 18.6 g of 5-oxo-1-(phenylmethyl)-N-(2-propyl)-3-pyrrolidinecarboxamide, mp 122°-124° C.

후처리

  1. temperaturecooled to room temperature
  2. customthe solvent removed in vacuo
  3. customthe residue partitioned between chloroform and water
  4. washThe organic layer was washed with water, 1N hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customto give 18.6 g

출처 및 근거

ORD 기록
ord-b7e33bcdd31f4a098cf30009b02a6cb1
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04550104

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