Triethylamine → HCID 54075416, compound

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.

1. distillationThe solvent was distilled off under reduced pressure
2. additionEthyl acetate was added to the residue
3. customthe solid so precipitated
4. filtrationwas filtered off
5. concentrationfollowed by concentration by evaporation under reduced pressure
6. dissolutionThe concentrate was then dissolved in 20 ml of chloroform
7. stirringby stirring at the same temperature for 2 hours
8. customAfter the completion of the reaction
9. concentrationthe reaction mixture was concentrated by evaporation under reduced pressure
10. washthe residue was subjected to chromatography on a silica gel column (eluting solvent: toluene/ethyl acetate=19/1)

ORD record

ord-c12c6b521d5345b1b7e237ad77c3c575

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06087379