1'-Benzyl-1H-spiro[furo[3,4-c]pyridine-3,4'-piperidine] → 1H-spiro[furo[3,4-c]pyridine-3,4'-piperidine]

HRID 1663340Notes

Reaction equation

HRID 1663340 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:16]=3[CH2:15][O:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1>FC(F)(F)CO.[Pd]>[NH:8]1[CH2:9][CH2:10][C:11]2([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:16]=3[CH2:15][O:14]2)[CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 597568161'-Benzyl-1H-spiro[furo[3,4-c]pyridine-3,4'-piperidine]

Product 1

HCID 467351631H-spiro[furo[3,4-c]pyridine-3,4'-piperidine]Yield 107.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 64092,2,2-TrifluoroethanolSolvent

Procedure

A solution of 0.22 g (0.78 mmol) 1′-benzyl-1H-spiro[furo[3,4-c]pyridine-3,4′-piperidine] in 8 ml 2,2,2-trifluoroethanol was purged with argon prior to adding 0.08 g (10 mol %) palladium on activated charcoal. The flask was evacuated, refilled with hydrogen gas and stirred under an atmosphere of hydrogen gas for 20 h. The catalyst was filtered off and washed with ethanol. The filtrate was concentrated to dryness to give the title compound (0.16 g, quantitative, purity of approximately 95%) as a light yellow amorphous solid.

Workup

  1. customThe flask was evacuated
  2. additionrefilled with hydrogen gas
  3. filtrationThe catalyst was filtered off
  4. washwashed with ethanol
  5. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-6918bb7117ee45529db37dfd26e8208c
Source dataset
uspto-grants-2011_10
Patent number
US08034937B2

Reaction notes

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