反应详情

In THF (60 ml) was dissolved 7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxylic acid (4.02 g). To the solution were added oxalyl chloride (1.99 ml) and a drop of DMF, and the mixture was stirred at room temperature for 1 hour and concentrated under reduced pressure. The residue was dissolved in THF (30 ml), and to the mixture was dropwise added a solution of 4-aminobenzyloxy-tert-butyldimethylsilane (3.97 g) and triethylamine (2.56 ml) in THF (30 ml) at room temperature. The reaction mixture was stirred at room temperature for 19 hours. To the mixture was added water (300 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/toluene/hexane=1/5/5). The resulting oil was dissolved in acetone (60 ml), and to the mixture was added 6N hydrochloric acid (2 ml). The mixture was stirred at room temperature for 30 minutes. To the reaction mixture were added 0.5% sodium hydroxide (500 ml) and diisopropylether (200 ml), and the mixture was stirred at room temperature for 5 minutes. The resulting precipitate s was filtered and recrystallized from acetone-diisopropylether to give N-[4-(hydroxy-methyl)phenyl]-7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamide (4.54 g) as pale brown crystals.

1. concentrationconcentrated under reduced pressure
2. dissolutionThe residue was dissolved in THF (30 ml)
3. additionto the mixture was dropwise added a solution of 4-aminobenzyloxy-tert-butyldimethylsilane (3.97 g) and triethylamine (2.56 ml) in THF (30 ml) at room temperature
4. additionTo the mixture was added water (300 ml)
5. extractionthe mixture was extracted with ethyl acetate
6. washThe organic layer was washed with saturated sodium chloride solution
7. dry with materialdried with anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was separated
10. custompurified with column chromatography (ethyl acetate/toluene/hexane=1/5/5)
11. dissolutionThe resulting oil was dissolved in acetone (60 ml)
12. additionto the mixture was added 6N hydrochloric acid (2 ml)
13. stirringThe mixture was stirred at room temperature for 30 minutes
14. additionTo the reaction mixture were added 0.5% sodium hydroxide (500 ml) and diisopropylether (200 ml)
15. stirringthe mixture was stirred at room temperature for 5 minutes
16. filtrationThe resulting precipitate s was filtered
17. customrecrystallized from acetone-diisopropylether