Hydrochloric Acid → (+/-)-(4R*,5R*)-5-carboxy-1-methyl4-phenylpyrrolidin-2-one

HRID 1838010Notes

Reaction equation

HRID 1838010 reaction equation
C([O:3][C:4]([C@@H:6]1[N:10]([CH3:11])[C:9](=[O:12])[CH2:8][C@@H:7]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:5])C.Cl>O>[C:4]([C@@H:6]1[N:10]([CH3:11])[C:9](=[O:12])[CH2:8][C@@H:7]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11379625(+/-)-(4R*,5R*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one

Product 1

HCID 12176379(+/-)-(4R*,5R*)-5-carboxy-1-methyl4-phenylpyrrolidin-2-oneYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(±)-(4R*,5R*)-5-(Ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one (16 g, 64.8 mmol), prepared according to the method of W. Hartwig and L. Born, J. Org. Chem., 52, 4352 (1987), was heated at the reflux temperature overnight in a 3:1 mixture of 3M HCl solution and water. The resulting mixture was allowed to cool to room temperature, extracted with EtOAc, dried (Na2SO4) and concentrated under reduced pressure. The crude product was triturated (Et2O) to give (±)-(4R*,5R*)-5-carboxy-1-methyl-4-phenylpyrrolidin-2-one (9.5 g, 67%): 1H NMR (CDCl3) δ 2.60 (dd, J=8.3, 16.0 Hz, 1H), 2.82-2.91 (m, 4H), 3.90 (q, J=8.9 Hz, 1H), 3.95 (br s, 1H), 4.37 (d, J=8.6 Hz, 1H), 7.19-7.32 (m, 5H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was triturated (Et2O)

Sources & evidence

ORD record
ord-57a7bfd4580c40fda191f558c67b4f4e
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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