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

HRID 50863Notes

Reaction equation

HRID 50863 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-49f1db4ac7094215b30574aa572eba69
Source dataset
uspto-grants-2004_03
Patent number
US06713492B1

Reaction notes

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