Potassium Carbonate → HCID 54383891, Verbindung

HRID 547235

Reaktionsgleichung

Reaktionsgleichung von HRID 547235
[CH3:1][N:2]([CH3:10])[C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1)=[O:4].Br[CH2:12][CH2:13][CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:15][CH2:14][CH2:13][CH2:12][N:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[C:3](=[O:4])[N:2]([CH3:10])[CH3:1]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 7408249(2S)-N,N-dimethylpyrrolidine-2-carboxamide

Produkt 1

HCID 54383891HCID 54383891, VerbindungAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of (S)-2-(N,N-dimethylcarbamoyl)pyrrolidine (426 mg, 3 mmol), (Chem. pharm. Bull. 1973, 21, 2112-2116), 3-bromo-1-propanol (0.41 ml, 4.5 mmol) and potassium carbonate (829 mg, 6 mmol) in acetonitrile (6 ml) was heated at reflux for 8 hours. The mixture was allowed to cool and was partitioned between methylene chloride and water. The organic layer was separated, washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography, eluting with methylene chloride/methanol (a gradient from 90/10 to 60/40) to give (S)-1-(3-hydroxypropyl)-2-(N,N-dimethylcarbamoyl)pyrrolidine (290 mg, 48%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 8 hours
  3. temperatureto cool
  4. customwas partitioned between methylene chloride and water
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed by evaporation
  9. customThe residue was purified by column chromatography
  10. washeluting with methylene chloride/methanol (a gradient from 90/10 to 60/40)

Quellen und Nachweise

ORD-Eintrag
ord-e9101b04e98e44efacaeb2d72ddc3fc7
Quelldatensatz
uspto-grants-2011_05
Patentnummer
USRE042353E1

Verknüpfte Notizen

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