Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate → 4-Oxo-piperidine-3-carboxylic acid ethyl ester

HRID 1773314Notes

Reaction equation

HRID 1773314 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9]1)C1C=CC=CC=1>CCO.[Pd]>[O:14]=[C:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 1

HCID 102624Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate

Product 1

HCID 1073164-Oxo-piperidine-3-carboxylic acid ethyl esterYield 88.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of ethyl 1-benzyl-4-oxopiperidine-3-carboxylate (360.0 g, 1.21 mol) in EtOH (6.7 L) was added wet Pd/C (55.0 g) under N2 that then was replaced by H2. The reaction mixture was stirred at rt for 4 h, filtered and concentrated to give a crude product. The crude product was slurried with EtOH (200 mL) for 2 h and then filtered. The filtered cake was washed with MTBE and the combined organic phases were concentrated to give the title compound (222.0 g, 1.07 mol, 88.4%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customto give a crude product
  4. filtrationfiltered
  5. washThe filtered cake was washed with MTBE
  6. concentrationthe combined organic phases were concentrated

Sources & evidence

ORD record
ord-e33d861d862540c89f7e6b56f0a739a1
Source dataset
uspto-grants-2016_02
Patent number
US09255096B1

Reaction notes

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