반응 #8854

반응 방정식

mesyl azide

tert-butyl 4-methoxy-4-(1,3-dioxopent-1-yl)piperidine-1-carboxylate

triethylamine

mesyl azide

sodium hydroxide

→

title compound

수율 70.8%

tert-Butyl 4-methoxy-4-(2-diazo-1,3-dioxopent-1-yl)piperidine-1-carboxylate

수율 70.8%

용매

dichloromethane

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.WAITAfter 2 h
2. 2
   추출extracted three times with dichloromethane
3. 3
   세척washed with saturated sodium chloride
4. 4
   건조dried over sodium sulfite
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The residue was purified by flash chromatography
8. 8
   세척eluting with 5% ethyl acetate/dichloromethane

실험 절차

To a solution of tert-butyl 4-methoxy-4-(1,3-dioxopent-1-yl)piperidine-1-carboxylate (0.227 g, 0.724 mmol) from Step C in dichloromethane (10 mL) was added triethylamine (0.101 mL, 0.724 mmol). Next, a solution of mesyl azide (0.087 g, 0.724 mmol) in dichloromethane (1 mL) was added. The reaction mixture was stirred for 3.5 h at room temperature. Additional mesyl azide (0.026 g, 0.217 mmol) was added. After 2 h, the reaction mixture was diluted with dichloromethane, poured into 1N sodium hydroxide solution, and extracted three times with dichloromethane. The organic layers were combined, washed with saturated sodium chloride, dried over sodium sulfite, filtered, and concentrated. The residue was purified by flash chromatography eluting with 5% ethyl acetate/dichloromethane to afford the title compound (0.174 g). MS/EI (acetonitrile/water): m/z 362 (M+Na) retention time=3.37 min.

출처