Dichloromethane → 1-Acetoxy-3-carbamoyl-2,2,5,5-tetramethylpyrrolidine

HRID 50863ノート

反応式

HRID 50863 の反応式
ClCCl.[OH:4][N:5]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]([C:12](=[O:14])[NH2:13])[C:6]1([CH3:16])[CH3:15].[C:17](OC(=O)C)(=[O:19])[CH3:18]>C(N(CC)CC)C>[C:17]([O:4][N:5]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]([C:12](=[O:14])[NH2:13])[C:6]1([CH3:16])[CH3:15])(=[O:19])[CH3:18]

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 922111-Hydroxy-2,2,5,5-tetramethylpyrrolidine-3-carboxamide

生成物 1

HCID 98374871-Acetoxy-3-carbamoyl-2,2,5,5-tetramethylpyrrolidine収率 86%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

20 ml of dichloromethane and 3 ml of triethylamine were added to 0.50 g (2.7 mmol) of 1-hydroxy-3-carbamoyl-2,2,5,5-tetramethylpyrrolidine. 0.38 ml (4.0 mmol) of acetic anhydride was added dropwise to the mixture with stirring and ice-cooling, the mixture was stirred for 3 hours. The reaction mixture was washed with water, 3% diluted hydrochloric acid, water, 5% sodium hydrogencarbonate aqueous solution, and water, in this order. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under vacuum. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from ethyl acetate to obtain 0.53 g (2.3 mmol) of white crystals (yield: 86%).

後処理

  1. temperatureice-cooling
  2. stirringthe mixture was stirred for 3 hours
  3. washThe reaction mixture was washed with water, 3% diluted hydrochloric acid, water, 5% sodium hydrogencarbonate aqueous solution, and water, in this order
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated under vacuum
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  7. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-49f1db4ac7094215b30574aa572eba69
出典データセット
uspto-grants-2004_03
特許番号
US06713492B1

反応ノート

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