HCID 86586605, compound → HCID 23447342, compound

HRID 2186173Notes

Reaction equation

HRID 2186173 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2([OH:28])[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25](Cl)[N:24]=[CH:23][N:22]=3)[CH2:17][CH2:16]2)[C:10](=[O:29])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2([OH:28])[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][N:22]=3)[CH2:17][CH2:16]2)[C:10](=[O:29])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86586605HCID 86586605, compound

Product 1

HCID 23447342HCID 23447342, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In ethanol (30 ml) was dissolved 4-(tert-butoxycarbonyl)-1-[1-(6-chloro-4-pyrimidinyl)-4-hydroxypiperidin-4-ylmethyl]piperazin-2-one (808 mg), and to the solution was added 10% palladium on carbon (containing 50% water, 242 mg). Under hydrogen atmosphere, the mixture was vigorously stirred overnight, and the catalyst was removed. The solvent was evaporated under reduced pressure, and the residue was purified with silica gel column chromatography (eluent:methanol/ethyl acetate=1/10) to give colorless amorphous of 4-(tert-butoxycarbonyl)-1-[4-hydroxy-1-(4-pyrimidinyl)piperidin-4-ylmethyl]piperazin-2-one (527 mg).

Workup

  1. customthe catalyst was removed
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified with silica gel column chromatography (eluent:methanol/ethyl acetate=1/10)

Sources & evidence

ORD record
ord-e7d3e7f43e934ee3bb7cd676e202893f
Source dataset
uspto-grants-2002_06
Patent number
US06403595B1

Reaction notes

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