2-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-4-(3-methyl-butyl)-piperazine-1-carboxylic acid tert-butyl ester → 2-(R)-(2-(R)-Amino-1-(S)-hydroxy-3-phenyl-propyl)-4-(3-methylbutyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1436506Notes

Reaction equation

HRID 1436506 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:10][C@@H:9]1[C@@H:19]([OH:42])[C@H:20]([N:28]=C(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:10][C@@H:9]1[C@@H:19]([OH:42])[C@H:20]([NH2:28])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 866153762-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-4-(3-methyl-butyl)-piperazine-1-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 690175222-(R)-(2-(R)-Amino-1-(S)-hydroxy-3-phenyl-propyl)-4-(3-methylbutyl)-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolve 2-(R)-[2-(R)-(benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-4-(3-methyl-butyl)-piperazine-1-carboxylic acid tert-butyl ester in methanol (3 mL) and add 10% palladium on carbon (29 mg). Stir under 1 atmosphere of hydrogen gas for 24 h and filter through a filtering agent, wash with methanol and concentrate to give the title compound which is used without further purification.

Workup

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

Sources & evidence

ORD record
ord-a8b8ea397b8944089664900d52b3afae
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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