Reacción #78925

Ecuación de reacción

triethylamine

amide

1-[1-(4-chloro-phenyl)-cyclobutanecarbonyl]-piperidin-3-ylmethyl alcohol

methanesulfonyl chloride

→

2

Rendimiento 71.0%

Methanesulfonic acid 1-[1-(4-chloro-phenyl)-cyclobutanecarbonyl]-piperidin-3-ylmethyl ester

Rendimiento 71.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat room temperature
2. 2
   Otroovernight
3. 3
   LavadoThe reaction mixture was washed successively with water, 1 N HCl, water, sat. sodium bicarbonate solution, and water (100 mL each)
4. 4
   SecadoThe organic layer was dried over anhydrous sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated by rotary evaporation
7. 7
   OtroThe residue was purified by chromatography on silica gel
8. 8
   Lavadoeluting with hexane/ethyl acetate (2:1)

Procedimiento

The amide derivative 1 (5.0 g, 16.3 mmol) was dissolved in dichloromethane (50 mL) and cooled to 0° C. To this solution was added triethylamine (5.0 mL) followed by dropwise addition of methanesulfonyl chloride (2.05 g, 17.9 mmol). The reaction was stirred at 0C for 1 h, and then at room temperature overnight. The reaction mixture was washed successively with water, 1 N HCl, water, sat. sodium bicarbonate solution, and water (100 mL each). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation. The residue was purified by chromatography on silica gel, eluting with hexane/ethyl acetate (2:1) to give 2 (4.45 g, 71%) as a tan gum; C18H24ClNO4S, LRMS (m/z)=386 (MH+).

Fuente