Toluene → Benzyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate

HRID 454483ノート

反応式

HRID 454483 の反応式
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1.[CH2:20]([O:27][C:28]1[CH:43]=[CH:42][C:41](Br)=[CH:40][C:29]=1[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(OCC)(=O)C.O>[CH2:20]([O:27][C:28]1[CH:43]=[CH:42][C:41]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:40][C:29]=1[C:30]([O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:31])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

参加物

10

反応物 4

HCID 1140TolueneHCID 8082Piperidine2 回HCID 10796Cesium carbonate2 回HCID 17750009Benzyl 2-(benzyloxy)-5-bromobenzoate

生成物 1

HCID 66990101Benzyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate

試薬・触媒・溶媒 5

HCID 167845palladium(II) acetate触媒2 回HCID 9811564Bis(dibenzylideneacetone)palladium触媒2 回HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl触媒2 回HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Piperidine (1.1 mL), cesium carbonate (4.9 g), tris(dibenzylideneacetone)dipalladium(0) (0.069 g), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.18 g), and palladium(II) acetate (0.034 g) were added to a toluene (30 mL) solution of benzyl 2-(benzyloxy)-5-bromobenzoate (3.0 g), followed by heating to reflux under a nitrogen atmosphere for 4 hours. The reaction mixture was cooled to room temperature, and then piperidine (0.37 mL), cesium carbonate (1.2 g), tris(dibenzylideneacetone)dipalladium(0) (0.069 g), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.18 g), and palladium(II) acetate (0.034 g) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 5 hours and 30 minutes. After cooling the reaction mixture to room temperature, water and ethyl acetate were added thereto, and the insoluble substance was removed by filtration. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-80% hexane/ethyl acetate] to obtain 2.4 g of benzyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate as a light yellow solid.

後処理

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 4 hours
  3. temperatureby heating
  4. temperatureto reflux under a nitrogen atmosphere for 5 hours and 30 minutes
  5. temperatureAfter cooling the reaction mixture to room temperature
  6. customthe insoluble substance was removed by filtration
  7. customThe organic layer was separated
  8. washwashed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-80% hexane/ethyl acetate]

出典と根拠

ORDレコード
ord-8d40576f157b4e8985baa3fe28727452
出典データセット
uspto-grants-2013_07
特許番号
US08492582B2

反応ノート

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