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

HRID 454483노트

반응식

HRID 454483 반응식
[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

참가 물질

10

반응물 4

HCID 1140TolueneHCID 8082Piperidine2회HCID 10796Cesium carbonate2회HCID 17750009Benzyl 2-(benzyloxy)-5-bromobenzoate

생성물 1

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

시약·촉매·용매 5

HCID 167845palladium(II) acetate촉매2회HCID 9811564Bis(dibenzylideneacetone)palladium촉매2회HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl촉매2회HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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]

출처 및 근거

ORD 기록
ord-8d40576f157b4e8985baa3fe28727452
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492582B2

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