Tropic acid → 3-Hydroxy-2-phenyl-1-pyrrolidin-1-yl propan-1-one

HRID 645480Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 645480
[C:1]([OH:12])(=O)[CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O>[OH:4][CH2:3][CH:2]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:1]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12]

Komponenten

7

Edukt 4

HCID 10726Tropic acidHCID 31268PyrrolidineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 687069803-Hydroxy-2-phenyl-1-pyrrolidin-1-yl propan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of tropic acid (0.12 mmol) and pyrrolidine (0.12 mmol) in DMF (20 mL) are added HOAt (0.18 mmol) and EDCI-HCl (0.18 mmol). The reaction mixture is stirred at room temperature for 14 h. The reaction mixture is diluted with water, then extracted with AcOEt. The organic extracts are successively washed with water, sat. aq, NaHCO3, H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is purified by silica gel column chromatography to give 3-hydroxy-2-phenyl-1-pyrrolidin-1-yl propan-1-one.

Aufarbeitung

  1. extractionextracted with AcOEt
  2. washThe organic extracts are successively washed with water
  3. dry with materialsat. aq, NaHCO3, H2O and brine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-15157d95db1648df88d50d6902912257
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07704996B2

Notizen zur Reaktion

Wird geladen…