1-Benzyloxycarbonyl-4-hydroxy-4-(4-benzyloxyphenyl)piperidine → 4-(4-Hydroxyphenyl)piperidin-4-ol

HRID 1675163Notes

Reaction equation

HRID 1675163 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([OH:31])[CH2:20][CH2:19][N:18](C(OCC3C=CC=CC=3)=O)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([OH:31])[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]2)=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 218398431-Benzyloxycarbonyl-4-hydroxy-4-(4-benzyloxyphenyl)piperidine

Product 1

HCID 110632814-(4-Hydroxyphenyl)piperidin-4-olYield 66.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (3.44 g, 3.23 mmol) was added to benzyl 4-[4-(benzyloxy)phenyl]-4-hydroxypiperidine-1-carboxylate (13.49 g, 32.31 mmol) in MeOH (146 mL). The resulting mixture was stirred at room temperature for 20 hours under an atmosphere of hydrogen. The reaction mixture was filtered and evaporated to afford crude product. The crude material was triturated with DCM (100 mL) and MeOH (50 mL) to give a solid which was collected by filtration and dried under vacuum to give 4-(4-hydroxyphenyl)piperidin-4-ol (4.16 g, 66.6%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. customto afford crude product
  4. customThe crude material was triturated with DCM (100 mL) and MeOH (50 mL)
  5. customto give a solid which
  6. filtrationwas collected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-a2d670071a9a43649afe73022356e1d3
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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