3-(2(S)-dibenzylamino-1-hydroxy-3-phenylpropyl)-4-benzyloxycarbonyl-1-methylpiperazin-2-one → 3-(2-(S)-amino-1-hydroxy-3-phenylpropyl)-1-methylpiperazin-2-one

HRID 1436492Notes

Reaction equation

HRID 1436492 reaction equation
C([N:8](CC1C=CC=CC=1)[C@@H:9]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:10]([CH:12]1[N:17](C(OCC2C=CC=CC=2)=O)[CH2:16][CH2:15][N:14]([CH3:28])[C:13]1=[O:29])[OH:11])C1C=CC=CC=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[NH2:8][C@@H:9]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:10]([CH:12]1[NH:17][CH2:16][CH2:15][N:14]([CH3:28])[C:13]1=[O:29])[OH:11]

Participants

5

Reactant 2

HCID 690173133-(2(S)-dibenzylamino-1-hydroxy-3-phenylpropyl)-4-benzyloxycarbonyl-1-methylpiperazin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 579388223-(2-(S)-amino-1-hydroxy-3-phenylpropyl)-1-methylpiperazin-2-one

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Treat a solution of 3-(2(S)-dibenzylamino-1-hydroxy-3-phenylpropyl)-4-benzyloxycarbonyl-1-methylpiperazin-2-one (Isomer-2) (210 mg, 0.36 mmol) in methanol (10 mL) with 20% palladium hydroxide on carbon (48 mg) in one portion and stir the mixture under 1 atmosphere of hydrogen gas for 24 h. Filter through a filtering agent, wash with methanol and concentrate to give the title compound as an oil.

Workup

  1. filtrationFilter through a filtering agent
  2. washwash with methanol
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-7570a1b369d4490b873edf535555a75e
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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