반응 #1605806

반응 방정식

benzyl 4-(3-amino-4-phenylphenyl)butyrate tosylate

pyridine

diphosgene

4-hydroxy-1-methylpiperidine

→

benzyl 4-[3-({[(1-methylpiperidin-4-yl)oxy]carbonyl}amino)-4-phenylphenyl]butyrate

수율 88.4%

용매

N,N-dimethylformamide

water

acetonitrile

반응 조건

후처리

1. 1
   workup.ADDITIONwas added, under ice-water cooling
2. 2
   농축the reaction mixture was concentrated under reduced pressure
3. 3
   기타to obtain a solid
4. 4
   기타The solid obtained
5. 5
   추출the reaction mixture was extracted with ethyl acetate
6. 6
   세척The organic layer was washed with a dilute aqueous solution of sodium hydroxide
7. 7
   건조a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
8. 8
   농축concentrated under reduced pressure
9. 9
   기타The residue was purified by flash column chromatography

실험 절차

Under a nitrogen flow, 4-hydroxy-1-methylpiperidine (10.4 g, 90.0 mmol) was dissolved in acetonitrile (100 mL) and to the solution was added, under ice-water cooling, a solution of diphosgene (35.6 g, 180 mmol) in acetonirile (50 mL) After stirring at room temperature for 5 hours, the reaction mixture was concentrated under reduced pressure to obtain a solid. The solid obtained was added to a solution of benzyl 4-(3-amino-4-phenylphenyl)butyrate tosylate (31.1 g, 60.0 mmol) in a mixed solvent of pyridine (50 mL) and N,N-dimethylformamide (150 mL), and the mixture was stirred at room temperature for 2 hours. Under ice-water cooling, the reaction was stopped by addition of purified water and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a dilute aqueous solution of sodium hydroxide and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain benzyl 4-[3-({[(1-methylpiperidin-4-yl)oxy]carbonyl}amino)-4-phenylphenyl]butyrate (25.8 g).

출처