Imidazole → 4(r)-Benzyl-3-(2-iodomethyl-3-methylbutyryl)oxazolidin-2-one

HRID 393698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 393698
[I:1]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[CH2:27]([C@@H:34]1[CH2:38][O:37][C:36](=[O:39])[N:35]1[C:40](=[O:47])[C@@H:41]([CH2:45]O)[CH:42]([CH3:44])[CH3:43])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[CH2:27]([C@@H:34]1[CH2:38][O:37][C:36](=[O:39])[N:35]1[C:40](=[O:47])[CH:41]([CH2:45][I:1])[CH:42]([CH3:44])[CH3:43])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 228882854-(R)-Benzyl-3-(2-(R)-hydroxymethyl-3-methylbutyryl)oxazolidin-2one

Produkt 1

HCID 228882814(r)-Benzyl-3-(2-iodomethyl-3-methylbutyryl)oxazolidin-2-oneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Iodine (42 g), triphenylphosphine (47 g) and imidazole (12 g) were added to a solution of 4-(R)-benzyl-3-(2-(R)-hydroxymethyl-3-methylbutyryl)oxazolidin-2-one (45 g) in toluene (400 ml) and the mixture was heated to 80° C. for 1 h, then cooled and washed with water and saturated brine. The solvent was dried (Na2SO4) and evaporated and the residue filtered through silica (200 g) eluting with diethyl ether-hexane 1:1 to give the title compound as a yellow viscous oil (56.4 g).

Aufarbeitung

  1. temperaturecooled
  2. washwashed with water and saturated brine
  3. dry with materialThe solvent was dried (Na2SO4)
  4. customevaporated
  5. filtrationthe residue filtered through silica (200 g)
  6. washeluting with diethyl ether-hexane 1:1

Quellen und Nachweise

ORD-Eintrag
ord-6b771874e35349ca944fce93f84052ae
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809100B2

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