反应详情

The compound (53.8 mg) obtained in Example 1-4 was dissolved in methanol (0.8 ml). Then, the solution was added with trimethyl orthoformate (50 μl), acetic acid (50 μl), N-Boc-D-prolinal (manufactured by Aldrich Corporation) (25.7 mg) and stirred at room temperature for 10 minutes. Subsequently, sodium cyanoborohydride (24.4 mg) was added, followed by stirring overnight at room temperature. The solvent was distilled off under reduced pressure and the residue was then dissolved in chloroform, followed by washing with 1 mol/l sodium hydroxide and saturated saline solution and drying with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/methanol). Then, the purified product was dissolved in methanol (500 μl) and added with a 4 mol/l hydrogen chloride/dioxane solution (500 μl), followed by stirring at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/methanol), thereby obtaining hydrochloride (33.9 mg) of the subject compound as a white solid.

1. stirringby stirring overnight at room temperature
2. distillationThe solvent was distilled off under reduced pressure
3. dissolutionthe residue was then dissolved in chloroform
4. washby washing with 1 mol/l sodium hydroxide and saturated saline solution
5. dry with materialdrying with anhydrous sodium sulfate
6. filtrationAfter filtration
7. distillationthe solvent was distilled off under reduced pressure
8. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)
9. dissolutionThen, the purified product was dissolved in methanol (500 μl)
10. additionadded with a 4 mol/l hydrogen chloride/dioxane solution (500 μl)
11. stirringby stirring at room temperature for 2 hours
12. customAfter completion of the reaction
13. distillationthe solvent was distilled off under reduced pressure
14. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)