Ethyl 4-amino-3-(3-chlorophenyl)butanoate → 4-(3-Chlorophenyl)pyrrolidin-2-one

HRID 1663562Notes

Reaction equation

HRID 1663562 reaction equation
[NH2:1][CH2:2][CH:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=1)[CH2:4][C:5](OCC)=[O:6]>C1(C)C=CC=CC=1>[Cl:16][C:12]1[CH:11]=[C:10]([CH:3]2[CH2:2][NH:1][C:5](=[O:6])[CH2:4]2)[CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 1

HCID 22387061Ethyl 4-amino-3-(3-chlorophenyl)butanoate

Product 1

HCID 179489414-(3-Chlorophenyl)pyrrolidin-2-oneYield 49.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 500 ml flask fitted with reflux condenser and magnetic stirrer, 135.7 g (561 mmoles) of ethyl 4-amino-3-(3-chlorophenyl)butanoate 378 are dissolved in 200 ml of toluene, and the mixture is refluxed for 30 min. The solution is concentrated to dryness and the residue purified by PrepLC (1 kg SiO2, CH2Cl2/EtOH, 98:2->95:5) to give 54.4 g of pure 379 (49.2%). GC/MS: 197/197 M+.

Workup

  1. customIn a 500 ml flask fitted
  2. temperaturewith reflux condenser and magnetic stirrer
  3. temperaturethe mixture is refluxed for 30 min
  4. concentrationThe solution is concentrated to dryness
  5. customthe residue purified by PrepLC (1 kg SiO2, CH2Cl2/EtOH, 98:2->95:5)

Sources & evidence

ORD record
ord-70bda6d25fbd4e3b8f6578409839c9ac
Source dataset
uspto-grants-2011_10
Patent number
US08034958B2

Reaction notes

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