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

HRID 50863Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 50863
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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-49f1db4ac7094215b30574aa572eba69
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713492B1

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