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

HRID 605821Notes

Reaction equation

HRID 605821 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-e2cd58920407428aa5a96140fd0c0a5f
Source dataset
uspto-grants-2011_03
Patent number
US07915261B2

Reaction notes

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