Water → HCID 21350204, compound

HRID 1359376Notes

Reaction equation

HRID 1359376 reaction equation
[CH2:1]([C:8]1[C:13]([O:14][CH2:15][O:16][CH3:17])=[CH:12][CH:11]=[C:10]([N:18]2[CH2:22][CH2:21][C@@H:20]([O:23]C(=O)C)[C:19]2=[O:27])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].O>CO>[CH2:1]([C:8]1[C:13]([O:14][CH2:15][O:16][CH3:17])=[CH:12][CH:11]=[C:10]([N:18]2[CH2:22][CH2:21][C@@H:20]([OH:23])[C:19]2=[O:27])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 21350202HCID 21350202, compound

Product 1

HCID 21350204HCID 21350204, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

453 mg of 2-benzyl-3-methoxymethyloxy-6-[(3R)-3-acetoxy-2-pyrrolidinone-1-yl]pyridine was dissolved in 5 ml of methanol, and two droplets of a 28% methanol solution of sodium methoxide was added thereto under stirring at room temperature, followed by stirring for 30 minutes. Then, water was added thereto, and the mixture was extracted with ethyl acetate. The organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The residue was subjected to separation and purification using silica gel column chromatography using 66% ethyl acetate/hexane as an eluent, to give 371 mg of the target compound.

Workup

  1. stirringby stirring for 30 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was further washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed
  6. customThe residue was subjected to separation and purification

Sources & evidence

ORD record
ord-e3bff283114247bd85aac0a9480cda8e
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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