Methyl iodide → 4-(6-Fluoropyridin-3-yl)-1-methylpyrrolidin-2-one

HRID 595923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595923
[F:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][NH:11][C:10](=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:17]>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][N:11]([CH3:17])[C:10](=[O:13])[CH2:9]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 1180464264-(6-Fluoropyridin-3-yl)pyrrolidin-2-one

Produkt 1

HCID 1180458344-(6-Fluoropyridin-3-yl)-1-methylpyrrolidin-2-oneAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 4-(6-fluoropyridin-3-yl)pyrrolidin-2-one (200 mg, 0.888 mmol) in DMF (4 mL) in ice bath was added NaH (42.6 mg, 1.066 mmol) and iodomethane (0.067 mL, 1.066 mmol). The reaction mixture was stirred in ice bath for 30 min and room temperature for 1 hour. LC-MS shows mixture of SM and product (1:1). Added again NaH (42.6 mg, 1.066 mmol) and iodomethane (0.067 mL, 1.066 mmol), stirred for 1 h at room temperature. Complete reaction by LC-MS. Reaction mixture was diluted with EtOAc and washed with water and bine. The organic layer was dried over sodium sulfate, filtered and evaporated. The crude was purified by flash chromatography [0-50-80% EtOAc (contains 10% MeOH)/heptane]. LCMS (m/z): 195.2 (MH+), 0.492 min. Yield 58%

Aufarbeitung

  1. waitroom temperature for 1 hour
  2. additionmixture of SM and product (1:1)
  3. stirringstirred for 1 h at room temperature
  4. customreaction by LC-MS
  5. customReaction mixture
  6. washwashed with water and bine
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude was purified by flash chromatography [0-50-80% EtOAc (contains 10% MeOH)/heptane]
  11. custom195.2 (MH+), 0.492 min

Quellen und Nachweise

ORD-Eintrag
ord-3e7af4c68f7e448aacdd99f4c591b64f
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242996B2

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