Tetrabutylammonium Fluoride → (R)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

HRID 1191512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191512
[Si]([O:8][CH2:9][C@H:10]([CH3:23])[CH2:11][N:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:22])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][C@H:10]([CH3:23])[CH2:11][N:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:22]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 68910127(R)-4-[3-(tert-Butyldimethylsilanyloxy)-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

Produkt 1

HCID 68910321(R)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-oneAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A reaction flask was charged with (R)-4-[3-(tert-Butyldimethylsilanyloxy)-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one (2.83 g, 8.5 mmol), and TBAF (11 mL, 1.0 M in THF, 11.0 mmol) in THF (10 mL) and stirred at rt for 20 h. The reaction mixture was concentrated, dissolved in EtOAc, and washed with brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 1:1) to give the title compound (1.72 g, 91%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in EtOAc
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-606355a71557450fb24b018d23cfb012
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680115B2

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