Methanol → HCID 58105236, compound

HRID 1668525Notes

Reaction equation

HRID 1668525 reaction equation
C(O[C:5]1[N:10]=[C:9]([C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[O:12])[C:8](C)=[CH:7][CH:6]=1)(=O)C.[OH-:27].[K+].[CH3:29]O>>[OH:27][CH2:29][C:5]1[N:10]=[C:9]([C:11]([N:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:17][CH2:18]2)=[O:12])[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 66852428HCID 66852428, compound

Product 1

HCID 58105236HCID 58105236, compound

Procedure

To a solution of 3.7 g of t-butyl 4-(6-acetoxy-methylpyridine-2-carbonyl)piperazine-1-carboxylate in 10 mL of methanol was added 840 mg of potassium hydroxide and the mixture was heated to reflux for 4 hours. After the solvent was removed, water was added to the solution and the mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, then the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel (methylene chloride-ethanol=50:1) to give 1.26 g of t-butyl 4-(6-hydroxymethylpyridine-2-carbonyl)piperazine-1-carboxylate as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. customAfter the solvent was removed
  4. additionwater was added to the solution
  5. extractionthe mixture was extracted with chloroform
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified by chromatography on silica gel (methylene chloride-ethanol=50:1)

Sources & evidence

ORD record
ord-674d46f773634acebc276e727f8ed9ac
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

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