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

HRID 1020984ノート

反応式

HRID 1020984 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
70 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-b0ef4dfe882e438688cfe9e89383896d
出典データセット
uspto-grants-2014_05
特許番号
US08716494B2

反応ノート

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