Methyl 4-benzyloxy-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoate → Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-hydroxybenzoate

HRID 644292Notes

Reaction equation

HRID 644292 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)[CH:10]=1)C1C=CC=CC=1>CCO.[Pd]>[C:29]([O:28][C:26]([N:23]1[CH2:24][CH2:25][CH:20]([O:19][C:11]2[CH:10]=[C:9]([OH:8])[CH:18]=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])[CH2:21][CH2:22]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 1

HCID 68532674Methyl 4-benzyloxy-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoate

Product 1

HCID 68532897Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-hydroxybenzoateYield 89.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The methyl 4-benzyloxy-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoate (12.8 g) was dissolved in EtOH (135 mL). 10% Pd/C catalyst (1.3 g) was added and the reaction was placed under an H2 atmosphere (4.1 bar) for 4 h at room temperature. The catalyst was filtered and the ethanol was removed in vacuo to give 9.15 g (89.7%) of a white foam.

Workup

  1. customfor 4 h
  2. customat room temperature
  3. filtrationThe catalyst was filtered
  4. customthe ethanol was removed in vacuo

Sources & evidence

ORD record
ord-edf06d4b0cc44177a8cd85cc27e6d173
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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