Arbaclofen → (R)-4-(4-Chlorophenyl)pyrrolidin-2-one

HRID 1799196Notes

Reaction equation

HRID 1799196 reaction equation
[CH:1]1[C:6]([C@H:7]([CH2:12][NH2:13])[CH2:8][C:9](O)=[O:10])=[CH:5][CH:4]=[C:3]([Cl:14])[CH:2]=1>C(O)(=O)C>[Cl:14][C:3]1[CH:4]=[CH:5][C:6]([C@@H:7]2[CH2:12][NH:13][C:9](=[O:10])[CH2:8]2)=[CH:1][CH:2]=1

Participants

3

Reactant 1

HCID 44602Arbaclofen

Product 1

HCID 1221679(R)-4-(4-Chlorophenyl)pyrrolidin-2-oneYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To R-baclofen (50 g, 234.7 mmol) was added 235 mL of acetic acid. The reaction mixture was refluxed overnight. The following day, the mixture was cooled to room temperature, the acetic acid removed in vacuo and the resultant mixture treated with water (400 mL). An off-white product precipitated and was filtered, washed with hexane, and dried in vacuo to provide the title compound as a white solid (42.1 g, 92% yield). 1H-NMR (400 MHz, CD3OD): δ7.22-7.33 m, 4H), 3.64-3.79 (m, 2H), 3.32-3.39 (m, 1H), 2.66-2.73 (dd, J=16.8, 8.8 Hz, 1H), 2.40-2.47 (dd, J=16.8, 8.8 Hz, 1H); MS (ESI) m/z 195.97 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customthe acetic acid removed in vacuo
  3. additionthe resultant mixture treated with water (400 mL)
  4. customAn off-white product precipitated
  5. filtrationwas filtered
  6. washwashed with hexane
  7. customdried in vacuo

Sources & evidence

ORD record
ord-693a421bf25744d4804743a13f9724ff
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Reaction notes

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