반응 #612654

반응 방정식

1-(6-hydroxy-naphthalen-2-ylmethyl)-piperidine-4-carboxylic acid ethyl ester

4-phenyl-cyclohexanol

triphenylphosphine

toluene

diisopropyl azodicarboxylate

→

product

수율 50.0%

ethyl 1-((6-((cis-4-phenylcyclohexyl)oxy)naphthalen-2-yl)methyl)piperidine-4-carboxylate

수율 50.0%

반응 조건

후처리

1. 1
   workup.STIRRINGThe solution was stirred
2. 2
   온도at reflux overnight
3. 3
   workup.ADDITIONThe reaction was added silica gel
4. 4
   농축the solvent was concentrated
5. 5
   기타The residue was purified with silica gel
6. 6
   세척eluted with EtOAc in hexanes from 0 to 20%

실험 절차

A mixture of 1-(6-hydroxy-naphthalen-2-ylmethyl)-piperidine-4-carboxylic acid ethyl ester (0.400 g, 1.28 mmol), 4-phenyl-cyclohexanol (0.2479 g, 1.406 mmol) and triphenylphosphine (0.6695 g, 2.553 mmol) in toluene (5 mL, 40 mmol) was stirred for 20 min, then diisopropyl azodicarboxylate (0.32 mL, 1.5 mmol) was added dropwise at 0° C. The solution was stirred at reflux overnight. The reaction was added silica gel and the solvent was concentrated. The residue was purified with silica gel eluted with EtOAc in hexanes from 0 to 20% to give product as an oil (0.3 g, 50%). LCMS: Rt=1.75 min, m/z=472.45 [M+H].

출처