Реакция #8855

Уравнение реакции

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

→

title compound

Выход 40.4%

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

Выход 40.4%

Растворители

hydrochloric acid

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture was refluxed for 45 min
2. 2
   Экстракцияextracted three times with dichloromethane
3. 3
   Промывкаwashed with saturated sodium chloride solution
4. 4
   Сушкаdried over sodium sulfite
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеThe residue was purified by flash chromatography
8. 8
   Промывкаeluting with 10% ethyl acetate/dichloromethane

Методика

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).

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