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

HRID 1199800노트

반응식

HRID 1199800 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-12180eb720814444ae587e899a1477ce
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04902801

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