HCID 54379876, compound → HCID 53687496, compound

HRID 2271002Notes

Reaction equation

HRID 2271002 reaction equation
C([N:8]1[CH2:13][C@@H:12]([CH2:14][CH:15]([CH3:17])[CH3:16])[N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][C@@H:9]1[CH2:25][O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)C1C=CC=CC=1>[Pd].CC(O)=O.[H][H]>[CH2:27]([O:26][CH2:25][C@H:9]1[CH2:10][N:11]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[C@H:12]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:13][NH:8]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 1

HCID 54379876HCID 54379876, compound

Product 1

HCID 53687496HCID 53687496, compoundYield 89.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

10% Palladium on carbon (0.8 g) was added to a solution of (2R,5R)-1-benzyl-2-benzyloxymethyl-4-(tert-butoxycarbonyl)-5-(2-methylpropyl)piperazine (8.1 g) in AcOH (80 ml), and the mixture was hydrogenated in hydrogen at 3 atm for 4 hours at ambient temperature. The catalyst was removed by filtration through a celite pad and the filtrate was washed with AcOH. The filtrate and combined washings were concentrated in vacuo, and the residue was partitioned by dissolving same in saturated aqueous NaHCO3 solution and AcOEt. The organic layer was washed with NaCl solution, dried over MgSO4, and concentrated in vacuo to give 5.8 g of (2R,5R)-2-benzyloxymethyl-4-(tert-butoxycarbonyl)-5-(2-methylpropyl)piperazine as an oil.

Workup

  1. customThe catalyst was removed by filtration through a celite pad
  2. washthe filtrate was washed with AcOH
  3. concentrationwere concentrated in vacuo
  4. customthe residue was partitioned
  5. dissolutionby dissolving same in saturated aqueous NaHCO3 solution
  6. washThe organic layer was washed with NaCl solution
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bcea065971ab451f915d5f12b0c0601c
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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