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

HRID 1173672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173672
[Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[C@@H:14]([CH3:15])[C@H:13]([O:16][Si](C(C)(C)C)(C)C)[C:12]([CH3:25])([CH3:24])[C:11]2=[O:26])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O>C1COCC1>[Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[C@@H:14]([CH3:15])[C@H:13]([OH:16])[C:12]([CH3:25])([CH3:24])[C:11]2=[O:26])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

5

Edukt 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 59557028Rac-2-chloro-4-[(4r,5s)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]benzonitrile

Produkt 1

HCID 59556917Rac-2-chloro-4-[(4r,5s)-4-hydroxy-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]benzonitrileAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of rac-2-chloro-4-[(4R,5S)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]benzonitrile (121 mg) in THF (5.5 mL) was added tetrabutylammonium fluoride-THF solution (0.5 mL, 1 mol/L), and the mixture was stirred at room temperature for 7 hr. Water was added to the reaction mixture, 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=10/1→1/2) to give the title compound as a colorless solid (yield: 47.2 mg, 55%).

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=10/1→1/2)

Quellen und Nachweise

ORD-Eintrag
ord-00b53039e20642ffb6c1d94be1d53e2b
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834051B2

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