5-hydroxy-4-propyldihydrofuran-2(3H)-one → HCID 15979801, Verbindung

HRID 2043697Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2043697
[F:1][C:2]1[CH:3]=[C:4]2[N:9]([C:10]=1[CH2:11][NH2:12])[CH:8]=[CH:7][CH:6]=[CH:5]2.O[CH:14]1[O:18][C:17](=O)[CH2:16][CH:15]1[CH2:20][CH2:21][CH3:22]>ClCCCl.ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[N:9]([C:10]=1[CH2:11][N:12]1[CH2:14][CH:15]([CH2:20][CH2:21][CH3:22])[CH2:16][C:17]1=[O:18])[CH:8]=[CH:7][CH:6]=[CH:5]2

Komponenten

5

Edukt 2

HCID 235310715-hydroxy-4-propyldihydrofuran-2(3H)-oneHCID 53629211HCID 53629211, Verbindung

Produkt 1

HCID 15979801HCID 15979801, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1-(2-fluoroindolizin-3-yl)methanamine x263 (0.38 g, 2.3 mmol) and 5-hydroxy-4-propyldihydrofuran-2(3H)-one x252 (0.33 g, 2.3 mmol) in DCE (12 ml) is kept at room temperature for 2 h, then STAB (0.74 g, 3.5 mmol) is added, and the mixture is stirred overnight. The reaction mixture is kept under stirring at 50° C. for 2 h, cooled to room temperature, and diluted with dichloromethane (10 ml). The mixture is washed with a 20% K2CO3 solution (2×15 ml), and the aqueous layer is washed with brine (25 ml), dried over anhydrous Na2SO4 and evaporated. The residue (0.60 g) is purified by chromatography on silica gel (gradient: chloroform to chloroform/methanol 50/1) to isolate a product of approximately 80% purity (0.162 g). This product is purified by chromatography on silicagel (hexane/ethyl acetate 5/2) to afford pure 1-[(2-fluoroindolizin-3-yl)methyl]-4-propylpyrrolidin-2-one 264 (0.126 g).

Aufarbeitung

  1. additionSTAB (0.74 g, 3.5 mmol) is added
  2. stirringunder stirring at 50° C. for 2 h
  3. washThe mixture is washed with a 20% K2CO3 solution (2×15 ml)
  4. washthe aqueous layer is washed with brine (25 ml)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated
  7. customThe residue (0.60 g) is purified by chromatography on silica gel (gradient: chloroform to chloroform/methanol 50/1)
  8. customto isolate a product of approximately 80% purity (0.162 g)
  9. customThis product is purified by chromatography on silicagel (hexane/ethyl acetate 5/2)

Quellen und Nachweise

ORD-Eintrag
ord-545f5111903e4edfb863a7c0416c7ec9
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586623B2

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