1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-(4-Fluorophenyl)-6-(2-methylallyl)-1,3-oxazinan-2-one

HRID 1640724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640724
Cl[CH2:2][CH2:3][C:4]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)([OH:9])[CH2:5][C:6]([CH3:8])=[CH2:7].BrC1C=CC=CC=1[C@@H]([N:26]=[C:27]=[O:28])C.C1CCN2C(=NCCC2)CC1>C1COCC1.CCOC(C)=O>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:4]2([CH2:5][C:6]([CH3:8])=[CH2:7])[O:9][C:27](=[O:28])[NH:26][CH2:2][CH2:3]2)=[CH:11][CH:12]=1

Komponenten

6

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 596356741-Chloro-3-(4-fluorophenyl)-5-methylhex-5-en-3-olHCID 86649409(S)-(-)-1-(-bromophenyl)ethyl isocyanate

Produkt 1

HCID 866494086-(4-Fluorophenyl)-6-(2-methylallyl)-1,3-oxazinan-2-oneAusbeute 65,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1-chloro-3-(4-fluorophenyl)-5-methylhex-5-en-3-ol (3.15 g, 13 mmol), (S)-(−)-1-(-bromophenyl)ethyl isocyanate (3.5 g, 16 mmol), and DBU (8 g, 33 mmol) in THF (80 mL) was heated to reflux for 25 h. The mixture was diluted with EtOAc and washed with 1 N aq HCl. The aqueous phase was extracted with EtOAc (3 x). The combined organic phase was dried over Na2SO4. After the solvents were evaporated, the crude product was purified by column to give (R)-3-(S)-1-(4-bromophenyl)-ethyl)-6-(4-fluorophenyl)-6-(2-methylallyl)-1,3-oxazinan-2-one (2.13 g, yield: 38%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 25 h
  3. washwashed with 1 N aq HCl
  4. extractionThe aqueous phase was extracted with EtOAc (3 x)
  5. dry with materialThe combined organic phase was dried over Na2SO4
  6. customAfter the solvents were evaporated
  7. customthe crude product was purified by column

Quellen und Nachweise

ORD-Eintrag
ord-9581f43c9722405aaf02ed7f6f8f4ef0
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08114868B2

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