Reaktion #8855

Reaktionsgleichung

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

→

title compound

Ausbeute 40.4%

tert-Butyl 4-oxo-3-(1-oxoprop-1-yl)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

Ausbeute 40.4%

Lösungsmittel

hydrochloric acid

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was refluxed for 45 min
2. 2
   Extraktionextracted three times with dichloromethane
3. 3
   Waschenwashed with saturated sodium chloride solution
4. 4
   Trocknendried over sodium sulfite
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by flash chromatography
8. 8
   Wascheneluting with 10% ethyl acetate/dichloromethane

Vorschrift

A solution of rhodium acetate dimer (0.002 g, 0.005 mmol) in dichloromethane (27 mL) was heated to 81° C. A solution of tert-butyl 4-methoxy-4-(2-diazo-1,3-dioxopent-1-yl)piperidine-1-carboxylate (0.092 g, 0.270 mmol) from Step D in dichloromethane (7 mL) was added slowly dropwise over 12 min. The reaction mixture was refluxed for 45 min then poured into IN hydrochloric acid, and extracted three times with dichloromethane. The organic layers were combined, washed with saturated sodium chloride solution, dried over sodium sulfite, filtered, and concentrated. The residue was purified by flash chromatography eluting with 10% ethyl acetate/dichloromethane to afford the title compound (0.034 g).

Quelle