Lithium Hydroxide → 1-(2,6-Dimethylphenyl)-3-(2-methylallyl)-5-oxo-pyrrolidine-3-carboxylic acid

HRID 2068249노트

반응식

HRID 2068249 반응식
C[O:2][C:3]([C:5]1([CH2:19][C:20]([CH3:22])=[CH2:21])[CH2:9][C:8](=[O:10])[N:7]([C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:18])[CH2:6]1)=[O:4].[Li+].[OH-]>CO>[CH3:17][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=1[N:7]1[C:8](=[O:10])[CH2:9][C:5]([CH2:19][C:20]([CH3:22])=[CH2:21])([C:3]([OH:4])=[O:2])[CH2:6]1

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 582187911-(2,6-Dimethylphenyl)-3-(2-methylallyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

생성물 1

HCID 670924761-(2,6-Dimethylphenyl)-3-(2-methylallyl)-5-oxo-pyrrolidine-3-carboxylic acid

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
70 °C

실험 절차

To a solution of 1-(2,6-dimethylphenyl)-3-(2-methylallyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (prepared from step a, 10.9 g, 36.21 mmol) in MeOH (100 mL) was added 1M LiOH (100 mL, 100 mmol) and the resulting clear solution was refluxed (70° C.) for an hour. The reaction mixture was then cooled to room temperature, MeOH was removed under reduced pressure and the obtained basic aqueous solution was added to a cooled (0° C.) 2N HCl (200 mL) with vigorous stirring. The resulting white solid was filtered, washed with water (3×300 mL), heptane (200 mL) and dried under high vacuum to obtain 1-(2,6-dimethylphenyl)-3-(2-methylallyl)-5-oxo-pyrrolidine-3-carboxylic acid (10 g, quantitative yield). LC-MS: Rt (retention time): 1.98 min, MS: (ES) m/z 288.1 (M+H+).

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customMeOH was removed under reduced pressure
  3. additionthe obtained basic aqueous solution was added to
  4. temperaturea cooled (0° C.) 2N HCl (200 mL) with vigorous stirring
  5. filtrationThe resulting white solid was filtered
  6. washwashed with water (3×300 mL), heptane (200 mL)
  7. customdried under high vacuum

출처 및 근거

ORD 기록
ord-88b49354762a4b1fb0258e98c77ca526
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293925B2

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