Réaction #5486

Équation de réaction

ammonium hydroxide

Methanesulfonic acid

2-Ethoxycarbonyl-cyclononanone

sodium azide

→

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

Solvants

chloroform

Conditions de réaction

Traitement

1. 1
   Températureheated
2. 2
   Températureto reflux for 4 hours
3. 3
   workup.ADDITIONThe reaction mixture is poured onto ice
4. 4
   Extractionextracted several times with methylene chloride
5. 5
   SéchageThe combined organic layers are dried (MgSO4)
6. 6
   Autrethe solvent is evaporated
7. 7
   AutreThe product is purified by silica gel chromatography (40% ethyl acetate/hexane)

Mode opératoire

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.

Source