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

HRID 978562Notes

Reaction equation

HRID 978562 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, 1N 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, 1N hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-eeb79e3ad3384fefba8c436d75f8a4a5
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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