Ethyl 3-(4-fluorophenyl)prop-2-enoate → (+/-)-trans-3-Ethoxycarbonyl-4(4'-fluorophenyl)piperidin-2,6-dione

HRID 1199800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1199800
[CH3:1][C:2](C)([O-:4])C.[K+].C[C:8]([NH:10]C(C([O-])=O)C([O-])=O)=[O:9].[F:18][C:19]1[CH:31]=[CH:30][C:22]([CH:23]=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=1>O1CCCC1.[Cl-].[Na+].O>[CH2:28]([O:27][C:25]([C@H:24]1[C@H:23]([C:22]2[CH:21]=[CH:20][C:19]([F:18])=[CH:31][CH:30]=2)[CH2:1][C:2](=[O:4])[NH:10][C:8]1=[O:9])=[O:26])[CH3:29]

Komponenten

6

Edukt 3

HCID 367200Ethyl 3-(4-fluorophenyl)prop-2-enoateHCID 21960945Ethyl amidomalonateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 11391819(+/-)-trans-3-Ethoxycarbonyl-4(4'-fluorophenyl)piperidin-2,6-dioneAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Potassium t-butoxide (1.01 g) was added to a solution of ethyl amidomalonate (1.38 g) in tetrahydrofuran (38 ml) maintained at 33°. After cooling to 25°, ethyl 4-fluorocinnamate (1.50 g) was added and the mixture stirred overnight at room temperature. Brine was added, the mixture extracted with ethyl acetate (3×60 ml) and the organic solution dried and evaporated to give the crude product. This was chromatographed on silica gel, using dry ether as eluent, to give the title compound (0.92 g, 43%), m.p. 97°-99°.

Aufarbeitung

  1. temperaturemaintained at 33°
  2. temperatureAfter cooling to 25°
  3. extractionthe mixture extracted with ethyl acetate (3×60 ml)
  4. customthe organic solution dried
  5. customevaporated
  6. customto give the crude product
  7. customThis was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-12180eb720814444ae587e899a1477ce
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04902801

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