Potassium Phosphate, Tribasic → Tert-butyl 3-pyridin-4-yl-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate

HRID 599351노트

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HRID 599351 반응식
FC(F)(F)S(O[C:7]1[CH2:13][CH:12]2[N:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:9]([CH2:10][CH2:11]2)[CH:8]=1)(=O)=O.CC1(C)C(C)(C)OB([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)O1.[Cl-].[Li+].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C1C(C2[C-]=CC=CC=2)=CC=CC=1)C.C1[C@H]2CC(PC3[C@H]4C[C@H](CC4)C3)[C@H](C2)C1.Cl[Pd+].C(OCC)(=O)C.O.O1CCOCC1>[N:35]1[CH:36]=[CH:37][C:32]([C:7]2[CH2:13][CH:12]3[N:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:9]([CH2:10][CH2:11]3)[CH:8]=2)=[CH:33][CH:34]=1

참가 물질

9

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 433294Lithium ChlorideHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 226480948-Boc-3-(trifluoromethylsulfonyloxy)-8-azabicyclo[3.2.1]oct-3-ene

생성물 1

HCID 67268174Tert-butyl 3-pyridin-4-yl-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate수율 57.2%

시약·촉매·용매 4

HCID 11272965[(1R,4S)-2-Bicyclo[2.2.1]heptanyl]-[(1S,4R)-2-bicyclo[2.2.1]heptanyl]phosphane;chloropalladium(1+);N,N-dimethyl-2-phenylaniline촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

1 g of tert-butyl 3-{[(trifluoromethyl)sulfonyl]oxy}-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate, 0.975 g of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 0.24 g of lithium chloride, 1.78 g of potassium phosphate, 0.157 g of 2′-(dimethylamino)-2-biphenylpalladium(II)chloride dinorbornylphosphine and 10 ml of dioxane are introduced into an 80 ml glass tube. The tube is sealed and then heated at 100° C. under microwave irradiation for 30 minutes. Water and ethyl acetate are added. The aqueous phase is extracted three times with ethyl acetate. The organic phases are combined and dried over sodium sulfate and the solvent is evaporated off under reduced pressure. The residue is chromatographed on silica gel with a mixture of heptane/ethyl acetate. 0.458 g of tert-butyl 3-pyridin-4-yl-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate is obtained.

후처리

  1. customThe tube is sealed
  2. extractionThe aqueous phase is extracted three times with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is evaporated off under reduced pressure
  5. customThe residue is chromatographed on silica gel with a mixture of heptane/ethyl acetate

출처 및 근거

ORD 기록
ord-d7bc2cbc67b743548d2b19506799ec94
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897773B2

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