Lawesson's reagent → Methyl 1-benzyl-5-thioxo-2-pyrrolidinecarboxylate

HRID 1394071Notes

Reaction equation

HRID 1394071 reaction equation
[CH2:1]([N:8]1[C:12](=O)[CH2:11][CH2:10][CH:9]1[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1>O1CCCC1>[CH2:1]([N:8]1[C:12](=[S:27])[CH2:11][CH2:10][CH:9]1[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 11096495Methyl 1-benzyl-5-oxo-2-pyrrolidinecarboxylate

Product 1

HCID 14759675Methyl 1-benzyl-5-thioxo-2-pyrrolidinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 1-benzyl-5-oxo-2-pyrrolidinecarboxylate (18.15 g, 77.8 mmol) and Lawesson's reagent (31.5 g, 77.9 mmol) were combined in dry tetrahydrofuran (100 mL) and stirred overnight at room temperature. The mixture was filtered, the filter cake was rinsed with tetrahydrofuran, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution. The organic phase was concentrated under reduced pressure and the residue was purified by chromatography on silica gel (3:1, hexanes:ethyl acetate) to provide the title compound. MS (ESI) m/z: 250 (M+H)+; 1H NMR (CDCl3) δ 2.17 (m, 1H), 2.27 (m, 1H), 3.15 (m, 2H), 3.69 (s, 3H), 4.30 (dd, 1H), 4.37 (d, 1H), 5.73 (d, 1H), 7.32 (m, 5H).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was rinsed with tetrahydrofuran
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with saturated sodium bicarbonate solution
  6. concentrationThe organic phase was concentrated under reduced pressure
  7. customthe residue was purified by chromatography on silica gel (3:1, hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-a36d320063f4451bb4a20f1f836c9ffb
Source dataset
uspto-grants-2008_03
Patent number
US07348343B2

Reaction notes

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