Sodium Methoxide → HCID 86656364, compound

HRID 1942518Notes

Reaction equation

HRID 1942518 reaction equation
[C:1]1([C@H:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C@H:8]2[C:20]([O:22][CH3:23])=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+]>CO>[C:1]1([C@H:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9][C@@H:8]2[C:20]([O:22][CH3:23])=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86656363HCID 86656363, compound

Product 1

HCID 86656364HCID 86656364, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-tert-Butyl 3-methyl (3S,4S)-4-phenylpiperidine-1,3-dicarboxylate (1.00 g) was dissolved in methanol (40 ml), and thereto was added sodium methoxide (1.0 M methanol solution, 4.70 ml), and the mixture was refluxed for 9 hours. The reaction mixture was cooled, and concentrated under reduced pressure. To the residue was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (the developing solvent: hexane/ethyl acetate=5/1) to give the title compound (585 mg).

Workup

  1. temperaturethe mixture was refluxed for 9 hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added a saturated aqueous ammonium chloride solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-ac25349e76824a3c9e1c6f1156a1c55d
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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