Urea → (R)-5-(Methoxymethyl)oxazolidin-2-one

HRID 650256Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 650256
[NH2:1]C(N)=O.[F-].[Ce+3].[F-].[F-].[CH3:9][O:10][CH2:11][C@H:12]1[CH2:16][O:15][C:14](=O)[O:13]1>CS(C)=O>[CH3:9][O:10][CH2:11][C@@H:12]1[O:13][C:14](=[O:15])[NH:1][CH2:16]1

Komponenten

5

Edukt 3

HCID 1176UreaHCID 24457Cerium trifluorideHCID 11007941(S)-(-)-4-(Methoxymethyl)-1,3-dioxolan-2-one

Produkt 1

HCID 15550531(R)-5-(Methoxymethyl)oxazolidin-2-oneAusbeute 82.972,703 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

Urea (246 g, 4.09 mmol) was dissolved in dimethyl sulfoxide (2.27 L), and thereto were added cerium fluoride (69.0 g, 0.454 mol) and (S)-4-methoxymethyl-1,3-dioxolan-2-one (600 g, 4.54 mol, optical purity 98.9%ee), in order. The mixture was stirred for 36 hours at 140° C. under an atmosphere of argon. After filtering off the insoluble materials, the filtrate was condensed in vacuo, and the residue was purified by distillation to give the subject (R)-5-methoxymethyloxazolidin-2-one (445 g, yield 74.7%, optical purity 98.6%ee).

Aufarbeitung

  1. filtrationAfter filtering off the insoluble materials
  2. customcondensed in vacuo
  3. distillationthe residue was purified by distillation

Quellen und Nachweise

ORD-Eintrag
ord-528ea58f7b5348a887c0f6364be9a941
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271388B1

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