4-(Aminomethyl)benzonitrile → (7aS,6S)-4-{[2-(3,5-dichloro-phenyl)-1,3-dioxo-hexahydro-pyrrolo[1,2-c]imidazol-6-ylamino]-methyl}-benzonitrile

HRID 49985

Reaktionsgleichung

Reaktionsgleichung von HRID 49985
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@H:12]3[CH2:15][C:16](=O)[CH2:17][N:11]3[C:10]2=[O:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:20]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1)#[N:21].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@H:12]3[CH2:15][C@H:16]([NH:27][CH2:26][C:25]4[CH:28]=[CH:29][C:22]([C:20]#[N:21])=[CH:23][CH:24]=4)[CH2:17][N:11]3[C:10]2=[O:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Komponenten

5

Edukt 3

HCID 826084-(Aminomethyl)benzonitrileHCID 5049666Sodium triacetoxyborohydrideHCID 21301015(7aS)-2-(3,5-dichloro-phenyl)-tetrahydro-pyrrolo[1,2-c]imidazole-1,3,6-trione

Produkt 1

HCID 21300996(7aS,6S)-4-{[2-(3,5-dichloro-phenyl)-1,3-dioxo-hexahydro-pyrrolo[1,2-c]imidazol-6-ylamino]-methyl}-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The compound of formula (In), wherein R11 is 4-cyano, m is 1, W=NH, and the bonds depicted as wavy bonds define the 7aS,6S stereoisomer, was prepared as follows. To a solution of (7aS)-2-(3,5-dichloro-phenyl)-tetrahydro-pyrrolo[1,2-c]imidazole-1,3,6-trione (0.5 g) (0.0017 mol) (Preparation 20), in 50 mL of DCM was added molecular sieves 4A, 4-cyanobenzyl amine (0.27 g) (0.002 mol), then NaBH(OAc)3 (0.54 g) (0.00255 mol.). The reaction mixture was stirred overnight at RT and then the insoluble material eliminated. After evaporating the solvent, the residue was purified by SiO2 chromatography (eluent: DCM/MeOH 98/2) to afford the titled compound and its stereoisomer. 7aS,6S stereoisomer (70 mg). NMR (CDCl3, 200 MHz): 7.45 (2H, d), 7.3 (1H, m), 7.2-7.1(4H, m), 4.25 (1H, dd), 4.05 (1H, d), 3.65 (2H, dd), 3.4(1H, m), 3.02 (1H, dd), 2.35-2.2 (1H, m), 2.0 (1H, bd).

Aufarbeitung

  1. customwas prepared
  2. customAfter evaporating the solvent
  3. customthe residue was purified by SiO2 chromatography (eluent: DCM/MeOH 98/2)

Quellen und Nachweise

ORD-Eintrag
ord-d36fbc0a06ef48a49fc3e81ba82b11d6
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710064B2

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