Tetrahydrofuran → 3-Pyridyl 4-(4-hydroxyphenoxy)-1-piperidinecarboxylate

HRID 2074269Notes

Reaction equation

HRID 2074269 reaction equation
C1COCC1.C([O:13][C:14]1[CH:35]=[CH:34][C:17]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[O:26])[CH2:21][CH2:20]2)=[CH:16][CH:15]=1)C1C=CC=CC=1.[H][H]>[C].[Pd].CC(O)C>[OH:13][C:14]1[CH:35]=[CH:34][C:17]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[O:26])[CH2:21][CH2:20]2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 670670553-Pyridyl 4-[4-(benzyloxy)phenoxy]-1-piperidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 670670763-Pyridyl 4-(4-hydroxyphenoxy)-1-piperidinecarboxylateYield 83.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

10% Palladium-carbon (catalytic amount) was added to a THF (75 ml)/2-propanol (75 ml) solution containing 3-pyridyl 4-[4-(benzyloxy)phenoxy]-1-piperidinecarboxylate (3.7 g), and in a hydrogen gas atmosphere, this was stirred at room temperature under normal pressure for 24 hours. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure, and the resulting solid was washed with EtOAc/hexane, and dried under reduced pressure to obtain 3-pyridyl 4-(4-hydroxyphenoxy)-1-piperidinecarboxylate (2.4 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washthe resulting solid was washed with EtOAc/hexane
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-f2b7b76f83854c9f9227e628704a9771
Source dataset
uspto-grants-2011_04
Patent number
US07919494B2

Reaction notes

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