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

HRID 907444Notes

Reaction equation

HRID 907444 reaction equation
[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

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 11575IodobenzeneHCID 2724141Tetrabutylammonium Fluoride

Product 1

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

Reagents, catalysts & solvents 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)CatalystHCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3202a8b2dbaf489a80ace91b344e8e53
Source dataset
uspto-grants-2011_09
Patent number
US08013157B2

Reaction notes

Loading…