Triethylamine → (4R,9aS)-4-(3,4,5-trifluorophenyl)-3,4,7,9a-tetrahydro-1H-pyrido[2,1-c][1,4]oxazin-6-one

HRID 553958Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553958
[C:1]([N:6]1[C@H:11]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([F:19])=[C:14]([F:20])[CH:13]=2)[CH2:10][O:9][CH2:8][C@@H:7]1/[CH:21]=[CH:22]/[C:23](OC)=O)(=[O:5])CC=C.C(N(CC)CC)C>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.ClCCl>[F:18][C:16]1[CH:17]=[C:12]([C@@H:11]2[CH2:10][O:9][CH2:8][C@@H:7]3[CH:21]=[CH:22][CH2:23][C:1](=[O:5])[N:6]23)[CH:13]=[C:14]([F:20])[C:15]=1[F:19]

Komponenten

5

Edukt 2

HCID 8471TriethylamineHCID 67463888methyl (E)-3-[(3S,5R)-4-(3-butenoyl)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]acrylate

Produkt 1

HCID 67464206(4R,9aS)-4-(3,4,5-trifluorophenyl)-3,4,7,9a-tetrahydro-1H-pyrido[2,1-c][1,4]oxazin-6-oneAusbeute 26,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178425456HCID 178425456, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Grubbs catalyst 2nd generation (285 mg) was added to a solution of methyl (E)-3-[(3S,5R)-4-(3-butenoyl)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]acrylate (1.24 g) in dichloromethane (100 mL), and the reaction solution was heated under reflux in a nitrogen atmosphere for 1.5 hours. The reaction solution was returned to room temperature. Triethylamine (3 mL) was added to the reaction solution, which was then stirred for 10 minutes. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to obtain 250 mg of the title compound. The property values of the compound are as follows.

Aufarbeitung

  1. temperaturethe reaction solution was heated
  2. temperatureunder reflux in a nitrogen atmosphere for 1.5 hours
  3. customwas returned to room temperature
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-e6342d256a5146a4adced94fc0b2907e
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048878B2

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