HCID 67309159, compound → HCID 10609421, compound

HRID 1253420Notes

Reaction equation

HRID 1253420 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-7cc8b3c84f7140e384721feb8d44f9e7
Source dataset
uspto-grants-2013_06
Patent number
US08455482B2

Reaction notes

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