2-(R)-(2-(S)-Dibenzylamino-1-(S)-hydroxy-3-phenylpropyl)-5,5-dimethylpyrrolidine-1-carboxylic acid tert-butyl ester → 2-(R)-(2-(S)-Amino-1-(S)-hydroxy-3-phenylpropyl)-5,5-dimethylpyrrolidine-1-carboxylic acid tert-butyl ester

HRID 732375Notes

Reaction equation

HRID 732375 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][C@@H:9]1[C@@H:15]([OH:39])[C@@H:16]([N:24](CC1C=CC=CC=1)CC1C=CC=CC=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][C@@H:9]1[C@@H:15]([OH:39])[C@@H:16]([NH2:24])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 688152432-(R)-(2-(S)-Dibenzylamino-1-(S)-hydroxy-3-phenylpropyl)-5,5-dimethylpyrrolidine-1-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 666977452-(R)-(2-(S)-Amino-1-(S)-hydroxy-3-phenylpropyl)-5,5-dimethylpyrrolidine-1-carboxylic acid tert-butyl esterYield 87%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Dissolve 2-(R)-(2-(S)-dibenzylamino-1-(S)-hydroxy-3-phenylpropyl)-5,5-dimethylpyrrolidine-1-carboxylic acid tert-butyl ester (182 mg, 0.34 mmol) in methanol (4 mL) and add 10% palladium hydroxide on carbon (43 mg). Stir under 1 atmosphere of hydrogen gas overnight and filter through a filtering agent, wash with methanol and concentrate to give the title compound as a colorless oil (103 mg, 87% yield).

Workup

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

Sources & evidence

ORD record
ord-1cb6c1ecb61540bb864f11eb14f5ac06
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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