Реакция #8845

Уравнение реакции

tert-butyl 2-(methoxycarbonyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate

tert-Butyl 2-(methoxycarbonyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate

lithium hydroxide

→

title compound

Выход 67.5%

tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate

Выход 67.5%

Растворители

ethanol tetrahydrofuran water

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   Температураto cool
3. 3
   Концентрированиеwas then concentrated
4. 4
   workup.DISSOLUTIONdissolved in water
5. 5
   Экстракцияdichloromethane, and extracted three times with dichloromethane
6. 6
   Промывкаwashed with brine
7. 7
   Сушкаdried over sodium sulfate
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated
10. 10
    Другоеto afford 11.4 g
11. 11
    ДругоеThe residue was purified by flash chromatography
12. 12
    Промывкаeluting with 20–30% ethyl acetate in hexanes

Методика

To a solution of tert-butyl 2-(methoxycarbonyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate (17.2 g, 0.055 mol) from Step F in a 2:2:1 mixture of ethanol/tetrahydrofuran/water (555 mL) was added pulverized lithium hydroxide (26 g, 1.10 mol). The reaction mixture was heated to 90° C. for 60 h. The reaction mixture was allowed to cool and was then concentrated, dissolved in water and dichloromethane, and extracted three times with dichloromethane. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 11.4 g. The residue was purified by flash chromatography eluting with 20–30% ethyl acetate in hexanes to give the title compound (9.41 g).

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