Tetrahydrofuran → HCID 67067094, compound

HRID 2074268Notes

Reaction equation

HRID 2074268 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-6f6229fbba7f407ba7cc6f95488e6fd7
Source dataset
uspto-grants-2011_04
Patent number
US07919494B2

Reaction notes

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