Cerium(III) chloride → 1,1-Dimethylethyl 3-ethylidene-4-hydroxy-1-piperidinecarboxylate

HRID 2288036Notes

Reaction equation

HRID 2288036 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10](=[CH:15][CH3:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[C:10](=[CH:15][CH3:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 54075416HCID 54075416, compound

Product 1

HCID 545398291,1-Dimethylethyl 3-ethylidene-4-hydroxy-1-piperidinecarboxylateYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.32 g (5.9 mmol) of 1-(t-butoxycarbonyl)-3-ethylidene-4-piperidone in 10 ml of methanol, 2.19 g (5.9 mmol) of cerium chloride 7 hydrate were added under ice cooling, followed by the addition of 0.22 g (5.9 mmol) of sodium borohydride. The resulting mixture was then stirred at room temperature for 1 hour. After removal of the solvent by distillation under reduced pressure, water was added to the residue, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The residue was subjected to chromatography on a silica gel column (eluting solvent: chloroform), whereby 1.33 g of 1-(t-butoxycarbonyl)-3-ethylidene-4-hydroxypiperidine were obtained in a quantitative yield as a colorless oil.

Workup

  1. customAfter removal of the solvent
  2. distillationby distillation under reduced pressure, water
  3. additionwas added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. washThe residue was subjected to chromatography on a silica gel column (eluting solvent: chloroform)

Sources & evidence

ORD record
ord-a1e0be5d0a8b41c081b592361d00553f
Source dataset
uspto-grants-2000_07
Patent number
US06087379

Reaction notes

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