Water → (5R)-5-[(4-tert-butylphenyl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

HRID 70543

Reaction equation

HRID 70543 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:12][O:13][C:14]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:15]=1[CH2:16][N:17]1[C@@H:21]([C:22]#[CH:23])[CH2:20][CH2:19][C:18]1=[O:24].O>C(N(CC)CC)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:23]#[C:22][C@@H:21]2[N:17]([CH2:16][C:15]3[CH:25]=[CH:26][C:27]([O:29][CH3:30])=[CH:28][C:14]=3[O:13][CH3:12])[C:18](=[O:24])[CH2:19][CH2:20]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 1420291-tert-Butyl-4-iodobenzeneHCID 58452699(5R)-1-(2,4-Dimethoxybenzyl)-5-ethynylpyrrolidin-2-one

Product 1

HCID 67398609(5R)-5-[(4-tert-butylphenyl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-oneYield 84%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Copper iodide (74 mg) and bis(triphenylphosphine)palladium(II) dichloride (135 mg) were added to a solution of 4-tert-butyliodobenzene (3.0 g) in triethylamine (10 mL), and the mixture was stirred at room temperature for 15 minutes. (5R)-1-(2,4-Dimethoxybenzyl)-5-ethynylpyrrolidin-2-one (1.0 g) was added thereto over one hour, and the mixture was stirred at room temperature for three hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→1:1) to give (5R)-5-[(4-tert-butylphenyl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one as a colorless powder (1.25 g, 84%).

Workup

  1. waitover one hour
  2. stirringthe mixture was stirred at room temperature for three hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was then evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→1:1)

Sources & evidence

ORD record
ord-b87af4f26a1349cb8f1f91571641531d
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Linked notes

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