HCID 12364536, compound → HCID 12364539, compound

HRID 522872Notes

Reaction equation

HRID 522872 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2[O:14][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:16][C:10]=2[CH2:9]1)C1C=CC=CC=1.[H][H]>CCO.[Pd]>[C:17]1([C:15]2[O:14][C:11]3[CH2:12][CH2:13][NH:8][CH2:9][C:10]=3[CH:16]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 12364536HCID 12364536, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12364539HCID 12364539, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-benzyl-2-phenyl-4,5,6,7-tetrahydrofuro[3, 2-c]pyridine (1.5 g, 0.00649 mol) in EtOH (30 mL) under nitrogen was added Pd—C(10%) (200 mg, 0.3 mmol). Hydrogen (1 atm) was applied and the reaction mixture was stirred for 3 to 4 h at RT. After consumption of starting materials as determined by TLC, the reaction mixture was filtered through Celite® (diatomaceous earth), washing with EtOH. The filtrate was concentrated to afford a solid which was washed with ether to afford 2-phenyl-4,5,6,7-tetrahydrofuro[3,2-c]pyridine (620 mg, 48%).

Workup

  1. customAfter consumption of starting materials
  2. filtrationthe reaction mixture was filtered through Celite® (diatomaceous earth)
  3. washwashing with EtOH
  4. concentrationThe filtrate was concentrated
  5. customto afford a solid which
  6. washwas washed with ether

Sources & evidence

ORD record
ord-c7137d4710fd4ef09a5cdc06c8796ff2
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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