Tetrahydrofuran → 1-Benzyl-4-phenyl-1,2,3,6-tetrahydropyridine

HRID 907444노트

반응식

HRID 907444 반응식
[CH2:1]1[CH2:5]OC[CH2:2]1.I[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9]C=1.CCCC[N+:17]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19]CC.[F-]>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(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:26]([N:17]1[CH2:18][CH:19]=[C:24]([C:25]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:7]=2)[CH2:23][CH2:22]1)[C:27]1[CH:28]=[CH:29][CH:5]=[CH:1][CH:2]=1

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 11575IodobenzeneHCID 2724141Tetrabutylammonium Fluoride

생성물 1

HCID 5636091-Benzyl-4-phenyl-1,2,3,6-tetrahydropyridine수율 90%

시약·촉매·용매 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)촉매HCID 8471Triethylamine용매

실험 절차

To a 4-mL vial, added 100 mg (0.28 mmol) (7) and 6 mg (0.0058 mmol) Pd2dba3-CHCl3. Next added 0.3 mL THF, 48 μL (0.43 mmol) iodobenzene, and finally 1.1 mL (1.1 mmol) TBAF solution (1M in THF). Let stir at room temperature for 18 hours. At the end of the reaction, added 200 μL triethylamine, let stir briefly, concentrated in vacuo, and purified the crude material directly by silica gel chromatography (automated column, 12 g SiO2, 0% to 20% EtOAc in hexanes gradient). Obtained 63 mg (90%) of 1-Benzyl-4-phenyl-1,2,3,6-tetrahydro-pyridine as a yellow oil.

후처리

  1. customAt the end of the reaction
  2. stirringlet stir briefly
  3. concentrationconcentrated in vacuo
  4. custompurified the crude material directly by silica gel chromatography (automated column, 12 g SiO2, 0% to 20% EtOAc in hexanes gradient)

출처 및 근거

ORD 기록
ord-3202a8b2dbaf489a80ace91b344e8e53
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013157B2

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