Hydrochloric Acid → 7-methyl-7-phenyl-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione

HRID 451102

Reaktionsgleichung

Reaktionsgleichung von HRID 451102
[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][C:3]1=[O:7].[C:14](Cl)([N:16]=[C:17]=[O:18])=[O:15].N#N.Cl>CCOC(C)=O>[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]2[O:7][C:17](=[O:18])[NH:16][C:14](=[O:15])[C:4]=2[CH2:5][CH2:6]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 119708Isocyanatocarbonyl chlorideHCID 3499412-Methyl-2-phenyl-cyclopentanone

Produkt 1

HCID 580755937-methyl-7-phenyl-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dioneAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
58 °C

Versuchsvorschrift

Combined 2-methyl-2-phenylcyclopentanone (Intermediate V(1) (705.5 mg, 4.05 mmol) and carbonisocyanatidic chloride (1700 mg, 8.06 mmol), flushed with N2, and sealed in a sealed tube. Heated at 58° C. for 1 h, then 130° C. for 1.75 h. Let cool to rt. Carefully opened the tube (HCl), and dissolved the residue in EtOAc. Partitioned with NaHCO3 (aq), and extracted 3 times into EtOAc. Washed combined organic layers with brine, dried over MgSO4, filtered, and concentrated in vacuo. Loaded the residue onto Silica gel and eluted with an EtOAc/Hexane gradient to afford 7-methyl-7-phenyl-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione (43% yield)LC-MS (M+H)+=244.1. 1H NMR (500 MHz, CDCl3) δ ppm 8.12 (1H, br. s.), 7.32-7.38 (2H, m), 7.26-7.30 (3H, m), 2.69-2.75 (2H, m), 2.43-2.52 (1H, m), 2.21-2.29 (1H, m), 1.68 (3H, s).

Aufarbeitung

  1. customsealed in a sealed tube
  2. temperatureLet cool to rt
  3. customPartitioned with NaHCO3 (aq)
  4. extractionextracted 3 times into EtOAc
  5. washWashed
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. washeluted with an EtOAc/Hexane gradient

Quellen und Nachweise

ORD-Eintrag
ord-e09ed1c7cc82418488eecc0238416a5f
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486952B2

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