3-Phenylprop-2-En-1-Ol → 2-(2-Morpholin-4-yl-2-oxo-ethyl)-2-(3-phenyl-allyl)-malonic acid diethyl ester

HRID 1830141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1830141
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:20](O)[CH:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH2:30]([O:32][C:33](=[O:49])[CH:34]([CH2:40][C:41]([N:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1)=[O:42])[C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH3:31].[H-].[Na+].B(F)(F)F>C1COCC1.C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:38]([O:37][C:35](=[O:36])[C:34]([CH2:40][C:41]([N:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1)=[O:42])([CH2:20][CH:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:33]([O:32][CH2:30][CH3:31])=[O:49])[CH3:39]

Komponenten

9

Edukt 5

HCID 3083-Phenylprop-2-En-1-OlHCID 6356Boron trifluorideHCID 11776TriphenylphosphineHCID 24758Sodium hydrideHCID 210257141,3-Diethyl 2-[2-(4-morpholinyl)-2-oxoethyl]propanedioate

Produkt 1

HCID 694346602-(2-Morpholin-4-yl-2-oxo-ethyl)-2-(3-phenyl-allyl)-malonic acid diethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of Pd(OAc)2 (17.5 mg, 0.078 mmol) and PPh3 (40.9 mg, 0.156 mmol) in dry THF (2 ml) under N2, cinnamyl alcohol (105.1 mg, 0.78 mmol) was added followed by a solution of 2-(2-morpholin-4-yl-2-oxo-ethyl)-malonic acid diethyl ester (250 mg, 0.87 mmol) and NaH (17.4 mg, 0.43 mmol) in dry THF (3 ml). BF3 (1M in THF, 1 ml, 1 mmol) was then added and the yellow solution was stirred at room temperature for 6.5 hours. The mixture was diluted with ethyl acetate (50 ml) and washed with 1N HCl (10 ml) and brine (2×20 ml). The organic layer was dried (MgSO4), concentrated in vacuum and purified by chromatography eluting with 1:1 v/v ethyl acetate-heptane mixture to give 2-(2-morpholin-4-yl-2-oxo-ethyl)-2-(3-phenyl-allyl)-malonic acid diethyl ester as a thick, yellow oil (266.5 mg, 85%); 1H NMR (CDCl3) 7.25 (m, 5H), 6.40 (d, J=15.6 Hz, 1H), 6.1 (dt, J=15.8, 7.7 Hz), 4.2 (q, J=7.1 Hz, 4H), 3.6 (m, 6H), 3.45 (m, 2H), 3.05 (d, J=7.6 Hz, 2H), 3.0 (s, 2H), 1.25 (t, J=7.1 Hz, 6H). MS: 404 (MH+)

Aufarbeitung

  1. washwashed with 1N HCl (10 ml) and brine (2×20 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuum
  4. custompurified by chromatography
  5. washeluting with 1:1 v/v ethyl acetate-heptane mixture

Quellen und Nachweise

ORD-Eintrag
ord-8d7c7fa14d554220bd6e905c0e105d62
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07064123B1

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