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Citric Acid → 1-(4-Fluorobenzoyl)-3-isopropyl-2-oxopyrrolidine-3-carbonitrile

HRID 714785
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 714785
[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([N:8]2[CH2:12][CH2:11][CH:10]([C:13]#[N:14])[C:9]2=[O:15])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].I[CH:21]([CH3:23])[CH3:22].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([N:8]2[CH2:12][CH2:11][C:10]([CH:21]([CH3:23])[CH3:22])([C:13]#[N:14])[C:9]2=[O:15])=[O:7])=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 114361891-(4-Fluorobenzoyl)-2-oxo-3-pyrrolidinecarbonitrile

Produkt 1

HCID 1178410181-(4-Fluorobenzoyl)-3-isopropyl-2-oxopyrrolidine-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of 1-(4-fluorobenzoyl)-2-oxopyrrolidine-3-carbonitrile (500 mg) obtained in Step F of Example 1 in N,N-dimethylformamide (5 mL) was added sodium hydride (60% in mineral oil, 130 mg) in an ice bath, and the mixture was stirred at the same temperature for 5 min. To the reaction mixture was added 2-iodopropane (1.1 mL) in an ice bath, and the mixture was stirred at 50° C. for 1 hr. To the reaction mixture was added 10% aqueous citric acid solution in an ice bath, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (310 mg).

Aufarbeitung

  1. stirringthe mixture was stirred at 50° C. for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-012d4172748e4d7f849cf8660f2e12c9
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09187453B2

Notizen zur Reaktion

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