HCID 14300313, compound → A85 4777

HRID 1761847Notes

Reaction equation

HRID 1761847 reaction equation
[OH:1][C:2]1[C:26]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:25][C:5]([C:6]([N:8]2[CH2:14][CH2:13][CH2:12][N:11](C(OCC3C=CC=CC=3)=O)[CH2:10][CH2:9]2)=[O:7])=[CH:4][C:3]=1[C:31]([CH3:34])([CH3:33])[CH3:32].[H][H]>[Pd].C(O)(=O)C>[OH:1][C:2]1[C:3]([C:31]([CH3:33])([CH3:32])[CH3:34])=[CH:4][C:5]([C:6]([N:8]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])=[CH:25][C:26]=1[C:27]([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 2

HCID 14300313HCID 14300313, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 3082813A85 4777

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 46.6 g (0.1 mol) of 1-(4-hydroxy-3,5-di-tert.-butylbenzoyl)-4-benzyloxycarbonylhomopiperazine (Example 1), 350 ml of glacial acetic acid and 2.3 g of palladium black is treated with hydrogen while stirring at 70°-80° C. for about 7 hours. The catalyst is then filtered off, and the solvent is removed by distillation under reduced pressure. The residue is dissolved in methylene chloride, and the solution is extracted by shaking with dilute sodium hydroxide solution and separated off. The organic phase is washed several times with water and then dried over anhydrous sodium sulfate. The residue left after the solvent has been removed in vacuo is recrystallized from acetonitrile with the addition of active charcoal.

Workup

  1. filtrationThe catalyst is then filtered off
  2. customthe solvent is removed by distillation under reduced pressure
  3. dissolutionThe residue is dissolved in methylene chloride
  4. extractionthe solution is extracted
  5. stirringby shaking with dilute sodium hydroxide solution
  6. customseparated off
  7. washThe organic phase is washed several times with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. waitThe residue left after the solvent
  10. customhas been removed in vacuo
  11. customis recrystallized from acetonitrile with the addition of active charcoal

Sources & evidence

ORD record
ord-f4b465d208cf495fbee4a2f9bf89f768
Source dataset
uspto-grants-1989_05
Patent number
US04829061

Reaction notes

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