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

HRID 50863노트

반응식

HRID 50863 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 98374871-Acetoxy-3-carbamoyl-2,2,5,5-tetramethylpyrrolidine수율 86%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-49f1db4ac7094215b30574aa572eba69
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713492B1

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