HCID 67309159, compound → HCID 10609421, compound

HRID 1010558Notes

Reaction equation

HRID 1010558 reaction equation
C(OC([N:11]1[CH2:15][C@H:14]([CH2:16][CH2:17][CH3:18])[C@H:13]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>[C].[Pd].C(O)C>[C:23]([O:22][C:20]([NH:19][C@H:13]1[C@@H:14]([CH2:16][CH2:17][CH3:18])[CH2:15][NH:11][CH2:12]1)=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 67309159HCID 67309159, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10609421HCID 10609421, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-propylpyrrolidine (4.02 g, 11.09 mmol) and a 10% palladium carbon catalyst (1.0 g) in ethanol (100 mL) was stirred hard for 20 hours under an ordinary pressure in a hydrogen atmosphere. Insoluble matter was removed through filtration by use of Celite, and then ethanol was removed under reduced pressure. The residue was dissolved in diethyl ether (200 mL), and the solution was washed by a 1 mol/L aqueous sodium hydroxide solution (100 mL), followed by drying over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, to thereby yield the title compound as a colorless oily substance (2.34 g, 92.4%).

Workup

  1. customInsoluble matter was removed through filtration by use of Celite
  2. customethanol was removed under reduced pressure
  3. dissolutionThe residue was dissolved in diethyl ether (200 mL)
  4. washthe solution was washed by a 1 mol/L aqueous sodium hydroxide solution (100 mL)
  5. dry with materialby drying over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ea510677d579492aac78414edbbd440a
Source dataset
uspto-grants-2011_07
Patent number
US07977327B2

Reaction notes

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