Water → Ethyl 1-methyl-5-oxo-3-phenyl-3-pyrroline-2-carboxylate

HRID 1837979Notes

Reaction equation

HRID 1837979 reaction equation
[CH3:1][N:2]([C:9](=[O:18])[C:10]#[C:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].O>C1COCC1.C(Cl)Cl>[CH3:1][N:2]1[C:9](=[O:18])[CH:10]=[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:3]1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 962WaterHCID 11390917ethyl 2-(N-methyl-3-phenylprop-2-ynoylamino)acetate

Product 1

HCID 11345577Ethyl 1-methyl-5-oxo-3-phenyl-3-pyrroline-2-carboxylateYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of ethyl 2-(N-methyl-3-phenylprop-2-ynoylamino)acetate (prepared according to the procedure described for Intermediate A, 20 g, 82 mmol) in THF (100 mL) was added a solution of Li(SiMe3)2 (1M in THF, 82 mL, 82 mmol). The resulting mixture was stirred for 2 h, then was slowly treated with water (20 mL) and diluted with CH2Cl2 (200 mL). The organic layer was washed with water (150 mL), a 1N HCl solution (150 mL) and water (150 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography (gradient from 0% to 50% EtOAc/hex) to give racemic ethyl 1-methyl-5-oxo-3-phenyl-3-pyrroline-2-carboxylate (14 g, 70%) as a brown oil: TLC (40% EtOAc/hex) Rf 0.13; 1H NMR (CDCl3) δ 1.10 (t, J=7.4 Hz, 3H), 3.03 (s, 3H), 4.12 (m, 2H), 5.13 (s, 1H), 6.46 (s, 1H), 7.39-7.41 (m, 3H), 7.53-7.60 (m, 2H); HPLC ES-MS m/z (rel abundance) 246 (MH+, 100%).

Workup

  1. washThe organic layer was washed with water (150 mL)
  2. dry with materiala 1N HCl solution (150 mL) and water (150 mL), dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by flash chromatography (gradient from 0% to 50% EtOAc/hex)

Sources & evidence

ORD record
ord-0fa179a95f044618b3dd6b8e93d7fd21
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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