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Phenylmethyl(2R,5S)-2-methyl-5-[(phenylamino)carbonyl]-1-piperidinecarboxylate → (3S,6R)-6-Methyl-N-phenyl-3-piperidinecarboxamide

HRID 2367415
Notes
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Reaction equation

HRID 2367415 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])[CH2:4][N:3]1C(OCC1C=CC=CC=1)=O>CCOC(C)=O.CCO.[Pd]>[CH3:1][C@H:2]1[NH:3][CH2:4][C@@H:5]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:9])[CH2:6][CH2:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 51357694Phenylmethyl(2R,5S)-2-methyl-5-[(phenylamino)carbonyl]-1-piperidinecarboxylate

Product 1

HCID 44174107(3S,6R)-6-Methyl-N-phenyl-3-piperidinecarboxamideYield 92.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of phenylmethyl(2R,5S)-2-methyl-5-[(phenylamino)carbonyl]-1-piperidinecarboxylate (21 g, 59.6 mmol) in EtOAc (250 mL) and EtOH (250 mL) was degassed. Pd/C (10%, 6.34 g, 5.96 mmol) was added and then H2 was bubbled through the mixture. The reaction mixture was stirred at room temperature under H2 balloon overnight. The mixture was filtered through a pad of celite, and concentrated in vacuo to afford the crude title compound (12 g). LC-MS (ES) m/z=219 [M+H]+.

Workup

  1. customH2 was bubbled through the mixture
  2. filtrationThe mixture was filtered through a pad of celite
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8faa386675014271937e00a79923e7c4
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08697685B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes