Hydrogen Bromide → 9-Bromonoscapine

HRID 1944984ノート

反応式

HRID 1944984 の反応式
[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

参加物

4

反応物 3

HCID 260Hydrogen BromideHCID 275196NoscapineHCID 178514845HCID 178514845、化合物

生成物 1

HCID 102550819-Bromonoscapine収率 82%

反応条件

温度
25 °C

実験手順

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.

後処理

  1. customSynthesis of 9-aminonoscapine

出典と根拠

ORDレコード
ord-770acea17ecb4bd78428b9eaa2955ce4
出典データセット
uspto-grants-2013_03
特許番号
US08394957B2

反応ノート

読み込み中…