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

HRID 5584

Reaktionsgleichung

Reaktionsgleichung von HRID 5584
[CH2:1]([O:3][C:4]([CH:6]=[C:7]1[C:13]2[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=2[N:11]([C:19](=[O:37])[C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[CH:22][C:21]=2[CH3:36])[CH2:10][CH2:9][CH2:8]1)=[O:5])[CH3:2].[BH4-].[Na+]>O1CCCC1.CO.O.O.O.O.O.O.[Ni](Cl)Cl>[CH2:1]([O:3][C:4]([CH2:6][CH:7]1[C:13]2[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=2[N:11]([C:19](=[O:37])[C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[CH:22][C:21]=2[CH3:36])[CH2:10][CH2:9][CH2:8]1)=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 542377055-ethoxycarbonylmethylidene-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Produkt 1

HCID 189173165-ethoxycarbonylmethyl-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepineAusbeute 43,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11791229Dichloronickel;hexahydrateKatalysatorHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture is further stirred for 10 minutes under ice-
  3. temperaturecooling
  4. filtrationThe insoluble materials are filtered with Celite
  5. concentrationthe filtrate is concentrated
  6. customThe resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-be3698e1a0504a98b5ed49a7b8e68b9f
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244898

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