反应详情

Triethylamine (0.2 mL, 1.4 mmol) was added to 3-(naphthalen-2-yl(phenoxy)methyl)azetidine hydrochloride (0.3 g, 0.92 mmol) dissolved in the methanol solution (20 mL), and stirred at room temperature for 1 hour. Formaldehyde (37% aqueous solution, 0.32 mL, 3.7 mmol), acetic acid (0.21 mL, 3.7 mmol) and sodium acetate borohydride (0.78 g, 3.7 mmol) were added in this order to the reaction mixture, and heated to reflux for one day. The temperature was reduced to room temperature, and 1N caustic soda solution (10 mL) was added thereto, followed by stirring for 30 minutes. The reaction mixture was extracted with methylene chloride, and the organic layer was washed with distilled water once, and then dried over anhydrous magnesium sulfate. The solvent was removed by reduced pressure evaporation to obtain a light yellow oily liquid, which was purified by flash chromatography (methylene chloride:methanol=9:1) to obtain a light yellow oily liquid (0.17 g).

1. temperatureheated
2. temperatureto reflux for one day
3. customwas reduced to room temperature
4. stirringby stirring for 30 minutes
5. extractionThe reaction mixture was extracted with methylene chloride
6. washthe organic layer was washed with distilled water once
7. dry with materialdried over anhydrous magnesium sulfate
8. customThe solvent was removed by reduced pressure evaporation
9. customto obtain a light yellow oily liquid, which
10. customwas purified by flash chromatography (methylene chloride:methanol=9:1)