5-Benzyl-4,5,6,7-tetrahydro-furo[3,2-c]pyridine → 4,5,6,7-Tetrahydrofuro[3,2-C]pyridine

HRID 2301111Notes

Reaction equation

HRID 2301111 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2[O:14][CH:15]=[CH:16][C:10]=2[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[O:14]1[C:11]2[CH2:12][CH2:13][NH:8][CH2:9][C:10]=2[CH:16]=[CH:15]1

Participants

5

Reactant 2

HCID 183773045-Benzyl-4,5,6,7-tetrahydro-furo[3,2-c]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 152899484,5,6,7-Tetrahydrofuro[3,2-C]pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Benzyl-4,5,6,7-tetrahydro-furo[3,2-c]pyridine (410 mg, 1.9 mmol) was dissolved in ethanol (4 ml), and the solution was mixed with 10% palladium on activated carbon (80 mg) and stirred at room temperature for 15 hours in an atmosphere of hydrogen. The reaction solution was filtered to remove 10% palladium on activated carbon, and the solvent was removed by evaporation under a reduced pressure to obtain crude 4,5,6,7-tetrahydro-furo[3,2-c]pyridine. This compound and 2a-(4-bromobutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (590 mg, 1.9 mmol) and potassium carbonate (400 mg, 2.9 mmol) were stirred at room temperature for 18 hours in anhydrous N,N-dimethylformamide (4 ml). The reaction solution was mixed with ethyl acetate, washed with water and saturated brine and then dried with anhydrous magnesium sulfate. The solvent was removed by evaporation from the organic layer under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 94 mg (0.27 mmol, 14% in yield) of the title compound.

Workup

  1. filtrationThe reaction solution was filtered
  2. customto remove 10% palladium on activated carbon
  3. customthe solvent was removed by evaporation under a reduced pressure

Sources & evidence

ORD record
ord-c755beee5e704e25b126e2b34dc2cf2e
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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