Methanol → Methyl (3S)-2-[(4-chlorobenzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate

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Reaction Steps

(3S)-2-[(4-Chlorobenzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2.08 g) is dissolved in methanol (30 ml) and thereto is added dropwise thionyl chloride (0.94 ml) at -20° C. The mixture is stirred at 50°-60° C. for 5 hours and then distilled to remove the solvent. The residue is dissolved in ethyl acetate, and the solution is washed with water, dried, treated with active carbon and distilled to remove the solvent. The residue is recrystallized from ethyl acetate-n-hexane to give the title compound (1.08 g, 50%) as colorless needles, mp 181°-182° C. (decomp.).

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