Methyl iodide → Methyl 1,2,3,4-tetrahydro-3-hydroxymethyl-beta-carboline-2-carbodithioate

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Reaction Conditions

Reaction Steps

(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).

Provenance & Evidence