HCID 68816363, compound → HCID 68817072, compound

HRID 732373Notes

Reaction equation

HRID 732373 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C@@H:13]([OH:37])[C@H:14]([N:22](CC1C=CC=CC=1)CC1C=CC=CC=1)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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[CH2:12][CH2:11][CH2:10][C@H:9]1[C@@H:13]([OH:37])[C@H:14]([NH2:22])[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 68816363HCID 68816363, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 68817072HCID 68817072, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Dissolve 2-(S)-[(2-(R)-dibenzylamino-1-(S)-hydroxy-3-phenylpropyl)]-pyrrolidine-1-carboxylic acid tert-butyl ester (610 mg, 1.2 mmol) in methanol (13 mL). Add 20% palladium hydroxide on carbon (157 mg). Bubble hydrogen gas through the mixture and stir under 1 atmosphere of hydrogen gas overnight. Bubble nitrogen through the mixture for 2 min, filter through a filtering agent, wash with methanol and concentrate to give the title compound (390 mg, 99%)

Workup

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

Sources & evidence

ORD record
ord-6b267a0acdff4f67a175a57c45bb6c04
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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