反应详情

160 mg of (2RS,3SR)-2-acetoxy-3-(3-hydroxy-4-phenoxyphenyl)-5-phenylpentane was dissolved in 5 ml of methanol, and 2.5 ml of a 1N sodium hydroxide aqueous solution was added, followed by stirring at room temperature for 3.5 hours. The reaction solution was concentrated under reduced pressure, and then, the residue was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The extract solution was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The drying agent was filtered off. The solvent was distilled off under reduced pressure, and the obtained residue was dissolved in 1 ml of methyl ethyl ketone. The solution was added to a suspension having 116 mg of potassium carbonate preliminarily suspended in 3 ml of methyl ethyl ketone, and 58 μl of benzyl bromide was further added at room temperature, followed by stirring under heating at 100° C. for 4 hours. The reaction solution was left to cool, then neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The extract solution was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The drying agent was filtered off. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to obtain 173 mg (yield: 96%) of the above identified compound as a colorless oily substance.

1. concentrationThe reaction solution was concentrated under reduced pressure
2. extractionextracted with ethyl acetate
3. washThe extract solution was washed with a saturated sodium chloride aqueous solution
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationThe drying agent was filtered off
6. distillationThe solvent was distilled off under reduced pressure
7. dissolutionthe obtained residue was dissolved in 1 ml of methyl ethyl ketone
8. additionThe solution was added to a suspension
9. addition58 μl of benzyl bromide was further added at room temperature
10. stirringby stirring
11. temperatureunder heating at 100° C. for 4 hours
12. waitThe reaction solution was left
13. temperatureto cool
14. extractionextracted with ethyl acetate
15. washThe extract solution was washed with a saturated sodium chloride aqueous solution
16. dry with materialdried over anhydrous sodium sulfate
17. filtrationThe drying agent was filtered off
18. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)
19. customto obtain 173 mg (yield: 96%) of the