Reacción #1454780

Ecuación de reacción

(1S,2S,4S)-4-(2-Chloro-benzenesulfonyl)-2-hydroxy-cyclopentanecarboxylic acid methyl ester

2,2,2-trichloro-acetimidic acid 1-(4-chloro-phenyl)-1-methyl-ethyl ester

NaHCO3

→

title compound

Rendimiento 32.0%

(1S,2S,4S)-4-(2-Chloro-benzenesulfonyl)-2-[1-(4-chloro-phenyl)-1-methyl-ethoxy]-cyclopentanecarboxylic acid methyl ester

Rendimiento 32.0%

Disolventes

DCM

DCM

cyclohexane

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture was extracted 3 times with ether
2. 2
   SecadoThe combined organic layers were dried (Na2SO4)
3. 3
   Otroevaporated
4. 4
   OtroThe remaining light yellow oil was purified by silica gel chromatography (heptane/EtOAc 4:1-3:1)

Procedimiento

(1R,2R,4R) and (1S,2S,4S)-4-(2-Chloro-benzenesulfonyl)-2-hydroxy-cyclopentanecarboxylic acid methyl ester (100 mg, 0.314 mmol, example 48, step 5) and 2,2,2-trichloro-acetimidic acid 1-(4-chloro-phenyl)-1-methyl-ethyl ester (270 mg, 0.514 mmol) were dissolved in a mixture of DCM (1 ml) and cyclohexane (2 ml). Then a solution of trifluoromethanesulfonic acid (0.836 μl, 0.00941 mmol) in DCM (0.1 ml) was added and the reaction mixture was stirred at room temperature for 6 h. Then saturated NaHCO3 solution was added and the mixture was extracted 3 times with ether. The combined organic layers were dried (Na2SO4) and evaporated. The remaining light yellow oil was purified by silica gel chromatography (heptane/EtOAc 4:1-3:1) to obtain the title compound (47 mg, 32%) as white solid. MS (EI): 488.1 (M+NH4)+.

Fuente