反応式
[OH:1][CH2:2][C@@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C@H:5]([CH3:16])[NH:4]1.[C:17](=[S:19])=[S:18].[CH2:20](N(CC)CC)C.CI>CS(C)=O>[OH:1][CH2:2][C@@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C@H:5]([CH3:16])[N:4]1[C:17]([S:19][CH3:20])=[S:18]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
実験手順
(1RS, 3RS)-cis-3-Hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-β-carboline (4.326 g) is dissolved in dimethylsulfoxide (20 ml), and thereto are added CS2 (2.4 ml) and triethylamine (5.6 ml). The mixture is stirred at room temperature for 30 minutes, and thereto is added dropwise methyl iodide (2.5 ml), and the mixture is stirred at room temperature for 2 hours. The reaction mixture is poured onto ice-water, and the mixture is extracted with ethyl acetate. The extract is washed with water, 5% HCl and water in order, dried over sodium sulfate and then distilled to remove the solvent. The residue is recrystallized from aqueous ethanol to give the title compound (5.5 g, 90%) as colorless needles, m.p. 164°-166° C., NMR (CDCl3, δ): 1.68 (d, J=6.8 Hz, 3H, C1 --CH3), 2.73 (s, 3H, CSSCH3); Mass m/e: 306 (M+), 258 (M+ --CH 3 SH).
後処理
- stirringthe mixture is stirred at room temperature for 2 hours
- additionThe reaction mixture is poured onto ice-water
- extractionthe mixture is extracted with ethyl acetate
- washThe extract is washed with water, 5% HCl and water in order
- dry with materialdried over sodium sulfate
- distillationdistilled
- customto remove the solvent
- customThe residue is recrystallized from aqueous ethanol
出典と根拠
- ORDレコード
- ord-332c494c01eb42aa973a21aa6f49dcd1
- 出典データセット
- uspto-grants-1986_09
- 特許番号
- US04612317
関連ノート
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