Triethylamine → HCID 54075416, compound

Participants

Reaction Steps

To a solution of 1.86 g (7.6 mmol) of the resulting 1-(t-butoxycarbonyl)-3-(1-hydroxyethyl)-4-piperidone in 20 ml of methylene chloride, 0.77 g (7.6 mmol) of triethylamine were added. To the resulting mixture, 0.88 g (7.6 mmol) of methanesulfonyl chloride were added under ice cooling, followed by stirring at room temperature for 1 hour. The solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue and the solid so precipitated was filtered off, followed by concentration by evaporation under reduced pressure. The concentrate was then dissolved in 20 ml of chloroform. To the resulting solution, 1.16 g (7.6 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was added at room temperature, followed by stirring at the same temperature for 2 hours. After the completion of the reaction, the reaction mixture was concentrated by evaporation under reduced pressure and the residue was subjected to chromatography on a silica gel column (eluting solvent: toluene/ethyl acetate=19/1), whereby 1.32 g (yield: 77.2%) of the title compound was obtained as a colorless oil.

Provenance & Evidence