Reacción #5486

Ecuación de reacción

ammonium hydroxide

Methanesulfonic acid

2-Ethoxycarbonyl-cyclononanone

sodium azide

→

ethyl 2-oxo-1-azacyclodecane-10-carboxylate

Disolventes

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturato reflux for 4 hours
3. 3
   workup.ADDITIONThe reaction mixture is poured onto ice
4. 4
   Extracciónextracted several times with methylene chloride
5. 5
   SecadoThe combined organic layers are dried (MgSO4)
6. 6
   Otrothe solvent is evaporated
7. 7
   OtroThe product is purified by silica gel chromatography (40% ethyl acetate/hexane)

Procedimiento

2-Ethoxycarbonyl-cyclononanone (13.72 g, 64.7 mmol) is dissolved in chloroform (200 mL) and cooled to 0° C. Methanesulfonic acid (62.4 g, 650 mmol) is added, followed by sodium azide (12.68 g, 195 mmol). The reaction is stirred at room temperature for 30 minutes, and then heated to reflux for 4 hours. The reaction mixture is poured onto ice, made basic with concentrated ammonium hydroxide (pH=9), and extracted several times with methylene chloride. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (40% ethyl acetate/hexane) to give ethyl 2-oxo-1-azacyclodecane-10-carboxylate, m.p. 101°-103° C.

Fuente