HCID 86586605, compound → HCID 23447342, compound

HRID 1840585Notes

Reaction equation

HRID 1840585 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-880043e5cde841a696eac3cf29516943
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

Loading…