Trifluoroacetic acid → (5R)-5-[(5-Chloro-6-methoxypyridin-2-yl)ethynyl]pyrrolidin-2-one

HRID 70536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 70536
FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:25]#[C:26][C@@H:27]2[N:31](CC3C=CC(OC)=CC=3OC)[C:30](=[O:43])[CH2:29][CH2:28]2)=[N:21][C:22]=1[O:23][CH3:24]>>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:25]#[C:26][C@@H:27]2[NH:31][C:30](=[O:43])[CH2:29][CH2:28]2)=[N:21][C:22]=1[O:23][CH3:24]

Komponenten

4

Edukt 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 58452822(5R)-5-[(5-Chloro-6-methoxypyridin-2-yl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

Produkt 1

HCID 58452568(5R)-5-[(5-Chloro-6-methoxypyridin-2-yl)ethynyl]pyrrolidin-2-oneAusbeute 82 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Trifluoroacetic acid (4 mL) and anisole (2 mL) were added to (5R)-5-[(5-chloro-6-methoxypyridin-2-yl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (457 mg), and the mixture was stirred at 80° C. for two hours. The reaction solution was concentrated, and the residue was diluted with chloroform, washed with saturated aqueous sodium bicarbonate and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1) to give the title compound as a colorless oil (234 mg, 82%).

Aufarbeitung

  1. concentrationThe reaction solution was concentrated
  2. additionthe residue was diluted with chloroform
  3. washwashed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1)

Quellen und Nachweise

ORD-Eintrag
ord-f892af96d00c421e9e067aca38e9ec4c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822503B2

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