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

HRID 553964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553964
[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(N1[C@H](C2C=C(F)C(F)=C(F)C=2)COC[C@@H]1/C=C\C(OC)=O)(=O)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

6

Edukt 3

HCID 8471TriethylamineHCID 67461698methyl (Z)-3-[(3S,5R)-4-(3-butenoyl)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]acrylateHCID 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 114,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178425456HCID 178425456, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Grubbs catalyst 2nd generation (27.7 mg) was added to a solution of methyl (E)-3-[(3S,5R)-4-(3-butenoyl)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]acrylate (109.8 mg) and methyl (Z)-3-[(3S,5R)-4-(3-butenoyl)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]acrylate (132.5 mg) in dichloromethane (12 mL), and the reaction solution was heated under reflux in a nitrogen atmosphere for one hour. The reaction solution was returned to room temperature. Triethylamine (0.5 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 (elution solvent: heptane:ethyl acetate=4:1->ethyl acetate) to obtain 96.6 mg of the title compound.

Aufarbeitung

  1. temperaturethe reaction solution was heated
  2. temperatureunder reflux in a nitrogen atmosphere for one hour
  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 (elution solvent: heptane:ethyl acetate=4:1->ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e924d50280184e98b1de8cb9c25905ad
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048878B2

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