Reacción #11572

Ecuación de reacción

diethylzinc

hexane

chloroiodomethane

(Z)-1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)-2-propenyl]urea

ammonium chloride

ammonium chloride

→

titled compound

Rendimiento 3.5%

cis-1-[2-(1-Adamantyl)ethyl]-1-pentyl-3-[2-(4-pyridyl)cyclopropylmethyl]urea

Rendimiento 3.5%

Disolventes

1,2-dichloroethane

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaice-cooling
2. 2
   Temperaturacooling
3. 3
   workup.STIRRINGthe whole was stirred at room temperature for 20 minutes
4. 4
   LavadoThe organic layer was washed with a saturated aqueous sodium chloride solution (10 ml)
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   OtroThe solvent was evaporated under reduced pressure
7. 7
   Otrothe resulting residue was purified by silica gel column chromatography

Procedimiento

A 1.0 M solution of diethylzinc in hexane (3.1 ml, 3.1 mmol) and chloroiodomethane (0.44 ml, 6.1 mol) were added to a solution of (Z)-1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)-2-propenyl]urea (Compound No. 1-111) in anhydrous 1,2-dichloroethane (3 ml) under a nitrogen atmosphere and ice-cooling, and the mixture was stirred for one hour. A saturated aqueous ammonium chloride solution (10 ml) was added to the reaction mixture under ice-cooling, and the whole was stirred at room temperature for 20 minutes and distributed with ethyl acetate (20 ml) and a saturated aqueous ammonium chloride solution (10 ml). The organic layer was washed with a saturated aqueous sodium chloride solution (10 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 9.0 mg (3.5%) of the titled compound as colorless crystals.

Fuente