Hydrogen Bromide → 9-Bromonoscapine

HRID 2408262

Reaktionsgleichung

Reaktionsgleichung von HRID 2408262
[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

Synthesis of 9-aminonoscapine was shown in Scheme 1. Briefly, noscapine (1) was dissolved minimum amount of 48% hydrobromic acid and then cautiously added freshly prepared bromine water. The reaction mixture stirred for 1 h at 25° C. and the resultant mixture was basified to pH 10 to afford 9-bromonoscapine in 82% yield. Refluxing compound 2 in DMF with sodium azide and sodium iodide for 15 hours gave its azido derivative (3) in quantitative yield. Reduction of azido derivative with tin chloride in the presence of thiophenol and triethylamine in THF for 2 h at 25° C. afforded the title compound, 9-aminonoscapine (4) in 83% yield.

Aufarbeitung

  1. customSynthesis of 9-aminonoscapine

Quellen und Nachweise

ORD-Eintrag
ord-5e3149f9152c45359925e37ddde9e5fb
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815835B2

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