反应详情

5.69 g of methyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride are suspended in 50 ml of chloroform, and 5.6 g of triethylamine are added thereto under ice-cooling and stirring. 3-benzoylthio-2-methylpropionyl chloride (which is prepared by heating a mixture of 5.6 g of 3-benzoylthio-2-methyl-propionic acid and 6 ml of thionyl chloride at 60° C. for 2 hours, followed by distillation thereof to remove the excess of thionyl chloride) is dissolved in 10 ml of tetrahydrofuran, and said tetrahydrofuran solution is added dropwise to the suspension obtained above. After the mixture is stirred at room temperature overnight, the chloroform layer is collected therefrom and washed with water, an aqueous sodium bicarbonate solution, diluted hydrochloric acid and water, successively. The chloroform solution is dried and then distilled to remove solvent. The residue thus obtained is purified by silica gel column chromatography (Solvent, toluene-ethyl acetate (4:1)). 8.0 g of methyl (3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate are obtained as colorless oil. Yield: 80.5 %

1. temperatureunder ice-cooling
2. temperatureby heating
3. distillationfollowed by distillation
4. customto remove the excess of thionyl chloride)
5. dissolutionis dissolved in 10 ml of tetrahydrofuran
6. additionis added dropwise to the suspension
7. customobtained above
8. stirringAfter the mixture is stirred at room temperature overnight
9. customthe chloroform layer is collected
10. washwashed with water
11. dry with materialThe chloroform solution is dried
12. distillationdistilled
13. customto remove solvent
14. customThe residue thus obtained
15. customis purified by silica gel column chromatography (Solvent, toluene-ethyl acetate (4:1))