Methyl iodide → HCID 67092407, compound

HRID 1020990Notes

Reaction equation

HRID 1020990 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:11][O:12][C:13]([C:15]1([CH2:29][O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[CH2:19][C:18](=[O:20])[N:17]([C:21]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:28])[CH2:16]1)=[O:14].I[CH3:41].[NH4+].[Cl-]>C1COCC1>[CH3:11][O:12][C:13]([C:15]1([CH2:29][O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[CH:19]([CH3:41])[C:18](=[O:20])[N:17]([C:21]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:28])[CH2:16]1)=[O:14]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 67092255HCID 67092255, compound

Product 1

HCID 67092407HCID 67092407, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LHMDS (1 M solution in THF, 2.32 mL, 2.32 mmol) was added slowly to a cooled (−50° C.) solution of 1-(2,6-dimethylphenyl)-3-(4-methoxybenzyloxymethyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (prepared from step a, 767 mg, 1.93 mmol) in THF (7 mL). After 5 min, iodomethane (602 μL, 9.65 mmol) was added at −50° C. and the resulting reaction mixture was warmed to room temperature and stirred further for 2 h. Saturated aqueous NH4Cl solution (25 mL) was added, and the solution was extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (75 mL), brine (75 mL), dried (Na2SO4) and evaporated. The residue was purified by flash chromatography (SiO2, 20→70% EtOAc/hexanes) to give 1-(2,6-dimethylphenyl)-3-(4-methoxybenzyloxymethyl)-4-methyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (736 mg, 93% yield). LC-MS: Rt (retention time): 2.39 min, MS: (ES) m/z 412.4 (M+H+).

Workup

  1. customthe resulting reaction mixture
  2. extractionthe solution was extracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with water (75 mL), brine (75 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography (SiO2, 20→70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2ea5664d50a9474abe0c72c95d53c6fd
Source dataset
uspto-grants-2014_05
Patent number
US08716494B2

Reaction notes

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