Potassium Carbonate → (S)-1-(3-hydroxypropyl)-2-(N,N-dimethylcarbamoyl)pyrrolidine

HRID 1838610Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1838610
[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 54383891(S)-1-(3-hydroxypropyl)-2-(N,N-dimethylcarbamoyl)pyrrolidineAusbeute 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-ae07fa032c524b73b809b2df9a7abb26
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06673803B2

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