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

HRID 1199800ノート

反応式

HRID 1199800 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-12180eb720814444ae587e899a1477ce
出典データセット
uspto-grants-1990_02
特許番号
US04902801

反応ノート

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