Methyl iodide → Methyl 1,2,3,4-tetrahydro-3-hydroxymethyl-beta-carboline-2-carbodithioate
Reaction equation
[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[CH2:5][NH:4]1.C(N(CC)CC)C.[C:23](=[S:25])=[S:24].[CH3:26]I>CO.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[CH2:5][N:4]1[C:23]([S:25][CH3:26])=[S:24]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
(3S)-3-Hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (30.3 g) is dissolved in a mixture of methanol (300 ml) and water (80 ml), and thereto are added triethylamine (15.9 g) and CS2 (11.9 g). The mixture is stirred at 20° C. for 30 minutes, and thereto is added dropwise methyl iodide (22.35 g). The mixture is stirred at 20°-25° C. for 1.5 hour and distilled to remove the solvent. The residue is dissolved in ethyl acetate and washed with 5% HCl and water, dried over sodium sulfate and distilled to remove the solvent. The residue is recrystallized from aqueous ethanol to give the title compound (42.0 g, 90%) as colorless needles, m.p. 114°-116° C., [α]D20 +159.0° (c=1, methanol). NMR (CDCl3, δ): 2.62 (s, 3H, CSSCH3), Mass m/e: 292 (M+), 244 (M+ --CH3SH).
Workup
- stirringThe mixture is stirred at 20°-25° C. for 1.5 hour
- distillationdistilled
- customto remove the solvent
- dissolutionThe residue is dissolved in ethyl acetate
- washwashed with 5% HCl and water
- dry with materialdried over sodium sulfate
- distillationdistilled
- customto remove the solvent
- customThe residue is recrystallized from aqueous ethanol
Sources & evidence
- ORD record
- ord-95d0f2d04a6b43a5b182e36835855c47
- Source dataset
- uspto-grants-1986_09
- Patent number
- US04612317
Reaction notes
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