4-Acetyl-2-(R)-[2-(R)-(benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl ester → 4-Acetyl-2-(R)-(2-(R)-amino-1-(S)-hydroxy-3-phenylpropyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1436504Notes

Reaction equation

HRID 1436504 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:16])[CH3:15])[CH2:10][C@@H:9]1[C@@H:17]([OH:40])[C@H:18]([N:26]=C(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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]([C:14](=[O:16])[CH3:15])[CH2:10][C@@H:9]1[C@@H:17]([OH:40])[C@H:18]([NH2:26])[CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 866153754-Acetyl-2-(R)-[2-(R)-(benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 690151434-Acetyl-2-(R)-(2-(R)-amino-1-(S)-hydroxy-3-phenylpropyl)-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolve 4-acetyl-2-(R)-[2-(R)-(benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl ester (66 mg, 0.12 mmol) in methanol (1 mL) and add 10% palladium on carbon (12 mg). Stir under 1 atmosphere of hydrogen gas overnight, filter through a filtering agent, wash with methanol and concentrate to give the title compound that may be used without further purification.

Workup

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

Sources & evidence

ORD record
ord-8ffc4e78d6ca49528663ad3e3419f1d5
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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