Tetrahydrofuran → HCID 67067094, compound

HRID 605820Notes

Reaction equation

HRID 605820 reaction equation
C1COCC1.C([O:13][C:14]1[CH:15]=[C:16]([CH:33]=[CH:34][CH:35]=1)[O:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[O:25])[CH2:20][CH2:19]1)C1C=CC=CC=1.[H][H]>[C].[Pd].CC(O)C>[OH:13][C:14]1[CH:15]=[C:16]([CH:33]=[CH:34][CH:35]=1)[O:17][CH:18]1[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[O:25])[CH2:22][CH2:23]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 67067073HCID 67067073, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67067094HCID 67067094, compoundYield 70.8%

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-[3-(benzyloxy)phenoxy]-1-piperidinecarboxylate (4.0 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-(3-hydroxyphenoxy)-1-piperidinecarboxylate (2.2 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-4a9af85be30440dba5183cdb4c2b463d
Source dataset
uspto-grants-2011_03
Patent number
US07915261B2

Reaction notes

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