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

HRID 1199800Notes

Reaction equation

HRID 1199800 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-12180eb720814444ae587e899a1477ce
Source dataset
uspto-grants-1990_02
Patent number
US04902801

Reaction notes

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