Tributyltin Chloride → (5R)-5-[(E)-2-(4-tert-Butylphenyl)-2-(tributylstannyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

HRID 70544Notes

Reaction equation

HRID 70544 reaction equation
[CH2:1]([Sn:5](Cl)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[C:15]([C:19]1[CH:24]=[CH:23][C:22]([C:25]#[C:26][C@@H:27]2[N:31]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=3[O:41][CH3:42])[C:30](=[O:43])[CH2:29][CH2:28]2)=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16]>O1CCCC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.[Cl-].[Cl-].[Pd+2]>[C:15]([C:19]1[CH:24]=[CH:23][C:22](/[C:25](/[Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:26]\[C@@H:27]2[N:31]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=3[O:41][CH3:42])[C:30](=[O:43])[CH2:29][CH2:28]2)=[CH:21][CH:20]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 2

HCID 15096Tributyltin ChlorideHCID 67398609(5R)-5-[(4-tert-butylphenyl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

Product 1

HCID 58452240(5R)-5-[(E)-2-(4-tert-Butylphenyl)-2-(tributylstannyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-oneYield 96%

Reagents, catalysts & solvents 2

HCID 11556747Bis(tricyclohexylphosphine)palladium(II) DichlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Bis(tricyclohexylphosphine)palladium(II) dichloride (230 mg) and tributyltin chloride (1.0 mL) were sequentially added to a solution of (5R)-5-[(4-tert-butylphenyl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (1.24 g) in tetrahydrofuran (15 mL) in a nitrogen gas stream, and the mixture was stirred at room temperature for two hours. The reaction solution was filtered through celite, and then the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→2:1) to give the title compound as a colorless powder (2.16 g, 96%).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→2:1)

Sources & evidence

ORD record
ord-81d195bbcfe6477f912fa5da07830412
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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