反应详情

To a mixture of (3R)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (6.49 g), KOH (3.5 g) and 50% ethanol (110 ml) is added dropwise carbon disulfide (1.82 ml) under ice-cooling. The mixture is stirred at room temprature for one hour, and thereto is added dropwise methyl iodide (2.5 ml). The mixture is further stirred at room temperature for 4 hours. The reaction mixture is distilled to remove the solvent. The residue is dissolved in water. The solution is acidified with 10% HCl and extracted with ethyl acetate. The extract is washed with water, dried and distilled to remove the solvent. The residue is purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=97:2:1), and the product is crystallized from aqueous ethanol to give the title compound (5.5 g, 60%), m.p. 103°-106° C. (decomp.).

1. temperaturecooling
2. stirringThe mixture is further stirred at room temperature for 4 hours
3. distillationThe reaction mixture is distilled
4. customto remove the solvent
5. dissolutionThe residue is dissolved in water
6. extractionextracted with ethyl acetate
7. washThe extract is washed with water
8. customdried
9. distillationdistilled
10. customto remove the solvent
11. customThe residue is purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=97:2:1)
12. customthe product is crystallized from aqueous ethanol