反应详情

(Step 3) To a solution of 1-[5-chloro-2-(methylsulfanyl)phenyl]methanamine hydrochloride obtained in Step 2 (5.11 g) and triethylamine (4.61 g) in tetrahydrofuran (150 ml) was added di-t-butyl dicarbonate (6.47 g) at room temperature. The mixture was stirred at the same temperature for 2 hr, treated with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in ethyl acetate (200 ml), and m-chloroperbenzoic acid (5.62 g, containing water: Wako Pure Chemical Industries, Ltd.) was added at 0° C. The mixture was stirred at the same temperature for 2 hr, and treated with aqueous sodium hydrogen carbonate solution. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=2:1). The obtained residue was dissolved in methanol (100 ml), and 4N hydrogen chloride-ethyl acetate solution (10 ml) was added. The mixture was stirred at 60° C. for 30 min, and concentrated under reduced pressure to give 1-[5-chloro-2-(methylsulfinyl)phenyl]methanamine hydrochloride (3.81 g) as a solid.

1. extractionextracted with ethyl acetate
2. washThe extract was washed with saturated brine
3. dry with materialdried over magnesium sulfate
4. customThe solvent was evaporated under reduced pressure
5. dissolutionThe obtained residue was dissolved in ethyl acetate (200 ml)
6. additionm-chloroperbenzoic acid (5.62 g, containing water: Wako Pure Chemical Industries, Ltd.) was added at 0° C
7. stirringThe mixture was stirred at the same temperature for 2 hr
8. additiontreated with aqueous sodium hydrogen carbonate solution
9. washThe organic layer was washed with saturated brine
10. dry with materialdried over magnesium sulfate
11. customThe solvent was evaporated under reduced pressure
12. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=2:1)
13. dissolutionThe obtained residue was dissolved in methanol (100 ml)
14. addition4N hydrogen chloride-ethyl acetate solution (10 ml) was added
15. stirringThe mixture was stirred at 60° C. for 30 min
16. concentrationconcentrated under reduced pressure