Imidazole → HCID 58218809, compound

HRID 2068257Notes

Reaction equation

HRID 2068257 reaction equation
N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:25]I.[CH3:27][O:28][C:29]([C:31]1([CH2:46]O)[CH:35]([CH3:36])[C:34](=[O:37])[N:33]([C:38]2[C:43]([CH3:44])=[CH:42][CH:41]=[CH:40][C:39]=2[CH3:45])[CH2:32]1)=[O:30]>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:27][O:28][C:29]([C:31]1([CH2:46][I:25])[CH:35]([CH3:36])[C:34](=[O:37])[N:33]([C:38]2[C:43]([CH3:44])=[CH:42][CH:41]=[CH:40][C:39]=2[CH3:45])[CH2:32]1)=[O:30]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 58218772HCID 58218772, compound

Product 1

HCID 58218809HCID 58218809, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Imidazole (261.5 mg, 3.84 mmol), triphenyiphosphine (670.7 mg, 2.56 mmol) and I2 (487.3 mg, 1.92 mmol) were added sequentially to a solution of 1-(2,6-dimethylphenyl)-3-hydroxymethyl-4-methyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (prepared from step c, 373 mg, 1.28 mmol) in toluene (15 mL) and resulting reaction mixture was heated at 100° C. with stirring for an hour. The reaction mixture was then cooled to room temperature and diluted with EtOAc (50 mL), washed with water (30 mL), saturated NH4Cl (30 mL), dried (Na2SO4) and evaporated. The residue was then purified by flash chromatography (SiO2, 20→70% EtOAc/hexanes) to obtain 1-(2,6-dimethylphenyl)-3-iodomethyl-4-methyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (427 mg, 83% yield). LC-MS: Rt (retention time): 2.32 min, MS: (ES) m/z 402.2 (M+H+).

Workup

  1. customresulting
  2. customreaction mixture
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. washwashed with water (30 mL), saturated NH4Cl (30 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was then purified by flash chromatography (SiO2, 20→70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-fa9a5d4ea5d4429fb6d2b62cc3559a7a
Source dataset
uspto-grants-2012_10
Patent number
US08293925B2

Reaction notes

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