1,1'-Carbonyldiimidazole → 1-Benzyl-N-cyclopropyl-5-oxopyrrolidine-3-carboxamide

HRID 464991Notes

Reaction equation

HRID 464991 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH:4]([C:14]([OH:16])=O)[CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:29]1([NH2:32])[CH2:31][CH2:30]1>C(#N)C>[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:5][CH:4]([C:14]([NH:32][CH:29]2[CH2:31][CH2:30]2)=[O:16])[CH2:3]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 69828CyclopropylamineHCID 990241-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid

Product 1

HCID 134918001-Benzyl-N-cyclopropyl-5-oxopyrrolidine-3-carboxamideYield 94.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 16.4 g (75 mmole) of 5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxylic acid in 150 ml of acetonitrile was added 13.8 g (85 mmole) of 1,1'-carbonyldiimidazole. The reaction was heated to 60° C. for one hour, cooled to room temperature and treated with 4.85 g (85 mmole) of cyclopropylamine. The reaction was stirred at room temperature for 18 hours, the solvent removed in vacuo and the residue partitioned between chloroform and water. The organic layer was washed with water, 1 N hydrochloric acid, dried over magnesium sulfate, filtered, and evaporated in vacuo to give 18.3 g of 5-oxo-1-(phenylmethyl)-N-cyclopropyl-3-pyrrolidinecarboxamide, mp 94°-96° C.

Workup

  1. temperaturecooled to room temperature
  2. customthe solvent removed in vacuo
  3. customthe residue partitioned between chloroform and water
  4. washThe organic layer was washed with water, 1 N hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-ede9ae2fb9ad4ecb932f380cf012a9b0
Source dataset
uspto-grants-1985_10
Patent number
US04550104

Reaction notes

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