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

Participants

Reaction Steps

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.

Provenance & Evidence