2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 58218772, compound

HRID 1020991Notes

Reaction equation

HRID 1020991 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:20][O:21]CC2C=CC(OC)=CC=2)[CH:9]([CH3:10])[C:8](=[O:11])[N:7]([C:12]2[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:19])[CH2:6]1)=[O:4].C(Cl)Cl.O.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([CH2:20][OH:21])[CH:9]([CH3:10])[C:8](=[O:11])[N:7]([C:12]2[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:19])[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 21908982Water methylene chlorideHCID 67092407HCID 67092407, compound

Product 1

HCID 58218772HCID 58218772, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a vigorously stirring mixture of 1-(2,6-dimethylphenyl)-3-(4-methoxy-benzyloxymethyl)-4-methyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (prepared from step b, 736 mg, 1.79 mmol) in 5:1 CH2Cl2/H2O (12 mL) was added 2,3-dichloro-5,6-dicyanobenzoquinone (609.5 mg, 2.68 mmol) at room temperature and stirred for 2 h at the same temperature. The reaction mixture was diluted with CH2Cl2 (25 mL) and filtered through celite, washed with CH2Cl2 (3×25 mL). The filtrate was then washed with saturated NaHCO3 solution (3×30 mL), water (30 mL), brine (30 mL), dried and evaporated. The obtained residue was purified by flash chromatography (SiO2, 20→70% EtOAc/hexanes) to give 1-(2,6-dimethylphenyl)-3-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (373 mg, 72% yield). LC-MS: R, (retention time): 1.2 min, MS: (ES) m/z 292.2 (M+H+).

Workup

  1. stirringstirred for 2 h at the same temperature
  2. filtrationfiltered through celite
  3. washwashed with CH2Cl2 (3×25 mL)
  4. washThe filtrate was then washed with saturated NaHCO3 solution (3×30 mL), water (30 mL), brine (30 mL)
  5. customdried
  6. customevaporated
  7. customThe obtained residue was purified by flash chromatography (SiO2, 20→70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6c63886638984429a7cfeb833b1409e4
Source dataset
uspto-grants-2014_05
Patent number
US08716494B2

Reaction notes

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