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

HRID 70544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 70544
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11556747Bis(tricyclohexylphosphine)palladium(II) DichlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-81d195bbcfe6477f912fa5da07830412
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822503B2

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