Reaktion #5684

Reaktionsgleichung

hydrochloric acid

5-ethoxycarbonylmethoxy-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

lithium borohydride

→

5-(2-hydroxyethoxy)-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Ausbeute 79.1%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture is refluxed for 30 minutes
2. 2
   Extraktionextracted with dichloromethane
3. 3
   TrocknenThe extract is dried over magnesium sulfate
4. 4
   workup.DISTILLATIONthe solvent is distilled off under reduced pressure
5. 5
   SonstigeThe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=100:1→50:1)
6. 6
   Sonstigerecrystallized from dichloromethane/diethyl ether

Vorschrift

To a solution of 5-ethoxycarbonylmethoxy-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (2.2 g) in tetrahydrofuran (50 ml) is added with stirring lithium borohydride (0.28 g) at room temperature, and the mixture is refluxed for 30 minutes. The reaction solution is poured into diluted hydrochloric acid and extracted with dichloromethane. The extract is dried over magnesium sulfate and the solvent is distilled off under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=100:1→50:1), and recrystallized from dichloromethane/diethyl ether to give 5-(2-hydroxyethoxy)-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.6 g) as white powder, mp. 185°-187.5° C.

Quelle