Sodium Carbonate → 3-(4-Fluorophenacyl)-1-(2-hydroxyethyl)pyrrolidine

HRID 1461740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1461740
[F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6](=[O:13])[CH2:7][CH:8]2[CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][OH:19].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:13])[CH2:7][CH:8]2[CH2:12][CH2:11][N:10]([CH2:17][CH2:18][OH:19])[CH2:9]2)=[CH:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 108982-BromoethanolHCID 110850303-(4-Fluorobenzoylmethyl)pyrrolidine

Produkt 1

HCID 148827083-(4-Fluorophenacyl)-1-(2-hydroxyethyl)pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 30.5 g of 3-(4-fluorophenacyl)pyrrolidine (Chem. Pharm. Bull., 1977, 25(8), p. 1911-1922), 19.4 g of 2-bromoethanol, 15.6 g of sodium carbonate and 400 ml of acetonitrile is heated to reflux for 6 hours. The mixture is concentrated, the residue is taken up in 150 ml of aqueous saline, the product is extracted 5 times with 150 ml of dichloromethane and this organic phase is dried over anhydrous sodium sulfate and concentrated. The oil obtained is purified by chromatography on 650 g of silica (70-230 mesh), using a mixture of dichloromethane, methanol and ammonia solution (96:4:0.4 V/V) as eluant. A colorless oil is obtained.

Aufarbeitung

  1. temperatureis heated
  2. temperatureto reflux for 6 hours
  3. concentrationThe mixture is concentrated
  4. extractionthe product is extracted 5 times with 150 ml of dichloromethane
  5. dry with materialthis organic phase is dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe oil obtained
  8. customis purified by chromatography on 650 g of silica (70-230 mesh)
  9. additiona mixture of dichloromethane, methanol and ammonia solution (96:4:0.4 V/V) as eluant
  10. customA colorless oil is obtained

Quellen und Nachweise

ORD-Eintrag
ord-90163f3eb6c34aa0b7597b26a6cc43ae
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05077288

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