Water → Rac-2-chloro-4-[(4r,5s)-4-hydroxy-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]-3-methylbenzonitrile

HRID 1967358Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1967358
[Si]([O:8][C@H:9]1[C@H:13]([CH3:14])[N:12]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([Cl:23])[C:16]=2[CH3:24])[C:11](=[O:25])[C:10]1([CH3:27])[CH3:26])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O>C1COCC1>[Cl:23][C:17]1[C:16]([CH3:24])=[C:15]([N:12]2[C@@H:13]([CH3:14])[C@H:9]([OH:8])[C:10]([CH3:27])([CH3:26])[C:11]2=[O:25])[CH:22]=[CH:21][C:18]=1[C:19]#[N:20]

Komponenten

5

Edukt 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 59556867Rac-4-((4r,5s)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl)-2-chloro-3-methylbenzonitrile

Produkt 1

HCID 59556873Rac-2-chloro-4-[(4r,5s)-4-hydroxy-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]-3-methylbenzonitrileAusbeute 55,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of rac-4-[(4R,5S)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]-2-chloro-3-methylbenzonitrile (103 mg) in THF (5 mL) was added tetrabutylammonium fluoride-THF solution (1.00 mL, 1 mol/L), and the mixture was stirred at room temperature for 17 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/3), and recrystallized from hexane-ethyl acetate to give the title compound as a colorless solid (yield: 41.4 mg, 28.4%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/3)
  6. customrecrystallized from hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-dab531acdccc4000b9bff66ebd321392
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420694B2

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