HCID 59756821, compound → HCID 59756818, compound

HRID 1665812Notes

Reaction equation

HRID 1665812 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][O:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1>[Pd].FC(F)(F)CO>[NH:8]1[CH2:9][CH2:10][C:11]2([C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][O:14]2)[CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 59756821HCID 59756821, compound

Product 1

HCID 59756818HCID 59756818, compoundYield 113%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 64092,2,2-TrifluoroethanolSolvent

Procedure

A 2-necked round bottom flask was charged with 0.56 g (2.0 mmol) 1′-benzyl-7H-spiro[furo[3,4-b]pyridine-5,4′-piperidine] and 20 ml 2,2,2-trifluoroethanol. The reaction mixture was purged with argon prior to adding 0.21 g (10 mol-%) palladium on activated charcoal. The flask was evacuated, refilled with hydrogen and stirred for 16 h. The catalyst was filtered off and washed with ethanol. The filtrate was concentrated to dryness to give the title compound (0.43 g, quantitative, purity of approx. 90%) as a light brown solid.

Workup

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

Sources & evidence

ORD record
ord-ae618c8c869e445fa93007c2e2a30907
Source dataset
uspto-grants-2011_10
Patent number
US08039624B2

Reaction notes

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