3-(3,5-Dichlorophenyl)-1-methylimidazolidine-2,4-dione → (1S*,4R*)-1-(4-Bromophenyl)-7-(3,5-dichlorophenyl)-5-methyl-5,7-diazaspiro[3.4]octane-6,8-dione

HRID 489231

Reaktionsgleichung

Reaktionsgleichung von HRID 489231
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Cl)[CH2:9][CH2:10]Br)=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:15]=[C:16]([N:21]2[C:25](=[O:26])[CH2:24][N:23]([CH3:27])[C:22]2=[O:28])[CH:17]=[C:18]([Cl:20])[CH:19]=1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@:24]3([C:25](=[O:26])[N:21]([C:16]4[CH:17]=[C:18]([Cl:20])[CH:19]=[C:14]([Cl:13])[CH:15]=4)[C:22](=[O:28])[N:23]3[CH3:27])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 119945103-(3,5-Dichlorophenyl)-1-methylimidazolidine-2,4-dioneHCID 123862481-Bromo-4-(3-bromo-1-chloropropyl)benzene

Produkt 1

HCID 60054870(1S*,4R*)-1-(4-Bromophenyl)-7-(3,5-dichlorophenyl)-5-methyl-5,7-diazaspiro[3.4]octane-6,8-dione

Versuchsvorschrift

Using the same procedure as in Example 1 starting from 1-bromo-4-(3-bromo-1-chloropropyl)benzene (Preparation 7) and 3-(3,5-dichlorophenyl)-1-methylimidazolidine-2,4-dione, the above titled compound was obtained after reverse phase HPLC purification (gradient from CH3CN/H2O/TFA: 5/95/0.05 to CH3CN/H2O/TFA: 80/20/0.05). 1H NMR (CDCl3): 7.44 (2H, d, J=8.4 Hz), 7.25 (1H, m), 6.95-7 (4H, m), 4.05 (1H, t, J=10.1 Hz), 3.22 (3H, s), 2.65-2.85 (1H, br q), 2.4-2.65 (2H, m), 2.1-2.3 (1H, br q).

Quellen und Nachweise

ORD-Eintrag
ord-f1e88edbaf794be7be0d0c8acbb077a8
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06977267B2

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