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

HRID 907444ノート

反応式

HRID 907444 の反応式
[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

参加物

6

反応物 3

HCID 8028TetrahydrofuranHCID 11575IodobenzeneHCID 2724141Tetrabutylammonium Fluoride

生成物 1

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

試薬・触媒・溶媒 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)触媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3202a8b2dbaf489a80ace91b344e8e53
出典データセット
uspto-grants-2011_09
特許番号
US08013157B2

反応ノート

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