Imidazole → (R)-4-(3-Iodo-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

HRID 1191514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191514
O[CH2:2][C@H:3]([CH3:16])[CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:41]I>C(Cl)Cl>[I:41][CH2:2][C@H:3]([CH3:16])[CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:15]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 68910321(R)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

Produkt 1

HCID 68908541(R)-4-(3-Iodo-2-methylpropyl]-4H-benzo[1,4]oxazin-3-oneAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A reaction flask was charged with (R)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one (1.71 g, 7.77 mmol), triphenylphosphine (4.50 g, 17.2 mmol), imidazole (1.27, 18.7 mmol), and iodine (5.54 g, 21.8 mmol) in CH2Cl2 (20 mL) and stirred at rt for 20 h. The reaction mixture was washed with saturated sodium thiosulfate, dried over Na2SO4, filtered, and concentrated. The product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 2:1) to give the title compound (2.25 g, 87%).

Aufarbeitung

  1. washThe reaction mixture was washed with saturated sodium thiosulfate
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-dbe9e68a9f6141b695176bbdf8f88477
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680115B2

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