Hydrogen Bromide → 9-Bromonoscapine

HRID 1968413

Reaktionsgleichung

Reaktionsgleichung von HRID 1968413
[CH3:1][N:2]1[C@@H:11]([C@H:12]2[O:21][C:19](=[O:20])[C:18]3[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=[CH:14][C:13]2=3)[C:10]2[C:9]([O:26][CH3:27])=[C:8]3[O:28][CH2:29][O:30][C:7]3=[CH:6][C:5]=2[CH2:4][CH2:3]1.[BrH:31].O.[Br]>>[CH3:1][N:2]1[C@@H:11]([C@H:12]2[O:21][C:19](=[O:20])[C:18]3[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=[CH:14][C:13]2=3)[C:10]2[C:9]([O:26][CH3:27])=[C:8]3[O:28][CH2:29][O:30][C:7]3=[C:6]([Br:31])[C:5]=2[CH2:4][CH2:3]1

Komponenten

4

Edukt 3

HCID 260Hydrogen BromideHCID 275196NoscapineHCID 178514845HCID 178514845, Verbindung

Produkt 1

HCID 102550819-BromonoscapineAusbeute 82 %

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Targetin was synthesized using a four-step synthetic scheme, as illustrated below. Noscapine (1) was brominated by adding 48% hydrobromic acid and freshly prepared bromine water. The reaction mixture was stirred for 1 hr at 25° C., and basified to pH 10 to yield 9-bromonoscapine (2) in ˜82% yield. Refluxing compound 2 in dimethyl formamide with sodium azide and sodium iodide for 15 hrs gave the corresponding azido derivative (3), which when reduced with tin chloride in the presence of thiophenol and triethylamine in tetrahydrofuran for 2 hrs at 25° C. to provide 9-aminonoscapine (4) in ˜83% yield.

Aufarbeitung

  1. customTargetin was synthesized

Quellen und Nachweise

ORD-Eintrag
ord-889d2a73c91f4c0191ea369640bb008f
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426398B2

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