Benzene → (R)-4-(6-Methoxynaphthalen-2-yl)-4-methyloxazolidin-2-one

HRID 2389040

Reaktionsgleichung

Reaktionsgleichung von HRID 2389040
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@H:13]([CH3:19])[CH2:14][O:15][C:16](=[O:18])[NH2:17])[CH:7]=[CH:6]2.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.[O-2].[Mg+2].C1C=CC=CC=1>CCOC(C)=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@:13]1([CH3:19])[CH2:14][O:15][C:16](=[O:18])[NH:17]1)[CH:7]=[CH:6]2

Komponenten

7

Edukt 4

HCID 241BenzeneHCID 6850729Magnesium monoxideHCID 12217721Iodo benzene diacetateHCID 67413984(S)-2-(6-Methoxynaphthalen-2-yl)propyl carbamate

Produkt 1

HCID 67414221(R)-4-(6-Methoxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 152122Dirhodium tetraacetateKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of carbamic acid (S)-2-(6-methoxy-naphthalen-2-yl)-propyl ester (5.4 g, 0.0208253 mol), iodobenzene diacetate (9.46 g, 0.0294 mol; Acros) and magnesium monoxide (1.93 g, 0.0479 mol; Aldrich), and rhodium(II) acetate dimer (500 mg, 0.001 mol; Janssen) in benzene (250 mL, 2.8 mol; Aldrich) was refluxed overnight under N2. TLC (EtOAc-hexanes 2:3) showed a slow moving spot. The solution was diluted with EtOAc and filtered through CELITE™ and washed with EtOAc and MeOH. Silica gel was added to the solution, which was then concentrated and purified on a 120 g silica gel column with 10-50% EtOAc/hexanes to give precipitate.

Aufarbeitung

  1. temperaturewas refluxed overnight under N2
  2. filtrationfiltered through CELITE™
  3. washwashed with EtOAc and MeOH
  4. additionSilica gel was added to the solution, which
  5. concentrationwas then concentrated
  6. custompurified on a 120 g silica gel column with 10-50% EtOAc/hexanes
  7. customto give precipitate

Quellen und Nachweise

ORD-Eintrag
ord-ebd265e2df474fcc9d523ebd8b0d0ce6
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08269043B2

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