Reaktion #5680

Reaktionsgleichung

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

sodium borohydride

→

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

Ausbeute 43.2%

Lösungsmittel

tetrahydrofuran methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.STIRRINGthe mixture is further stirred for 10 minutes under ice-
3. 3
   Temperaturcooling
4. 4
   FiltrationThe insoluble materials are filtered with Celite
5. 5
   Einengenthe filtrate is concentrated
6. 6
   SonstigeThe resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:1)

Vorschrift

5-Ethoxycarbonylmethylidene-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.30 g) and nickel chloride hexahydrate (0.55 g) are dissolved in a mixture of tetrahydrofuran/methanol (1:1) (30 ml), and to the mixture is added slowly sodium borohydride (0.26 g) with stirring under ice-cooling, and then the mixture is further stirred for 10 minutes under ice-cooling. The insoluble materials are filtered with Celite, and the filtrate is concentrated. The resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:1) to give 5-ethoxycarbonylmethyl-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.13 g) as colorless amorphous.

Quelle