Reacción #44995

Ecuación de reacción

Trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid

sodium hydrogen carbonate

1-hydroxybenzotriazole

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

N,N,N′-trimethylethylenediamine

→

methyl trans-4-{[[2-(dimethylamino)ethyl](methyl)amino]carbonyl}-cyclohexanecarboxylate

Rendimiento 93.3%

Disolventes

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   Extracciónthe mixture is extracted with chloroform
3. 3
   LavadoThe organic layer is washed with saturated brine
4. 4
   Secadodried over sodium sulfate
5. 5
   ConcentraciónThe solvent is concentrated under reduced pressure
6. 6
   OtroThe resulting residue is purified by silica gel column chromatography (eluent: chloroform/methanol/28% ammonia water=200/10/1)

Procedimiento

Trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (8.84 g) obtained in Reference Example 1(2) is dissolved in chloroform (100 ml), and thereto are added 1-hydroxybenzotriazole (7.14 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (10.00 g) and N,N,N′-trimethylethylenediamine (5.33 g) under ice-cooling. The mixture is then stirred at room temperature for 4 hours. Saturated aqueous sodium hydrogen carbonate solution is poured to the reaction solution and the mixture is extracted with chloroform. The organic layer is washed with saturated brine and dried over sodium sulfate. The solvent is concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: chloroform/methanol/28% ammonia water=200/10/1) to give methyl trans-4-{[[2-(dimethylamino)ethyl](methyl)amino]carbonyl}-cyclohexanecarboxylate (11.98 g).

Fuente