Реакция #8861

Уравнение реакции

tert-butyl 1-(1-hydroxyprop-1-yl)-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate

tert-Butyl 1-(1-hydroxyprop-1-yl)-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate

Jones reagent

→

title compound

Выход 66.7%

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

Выход 66.7%

Растворители

acetone

Условия реакции

Обработка

1. 1
   Другоеwas then quenched with isopropanol
2. 2
   workup.ADDITIONThe mixture was diluted with water
3. 3
   Экстракцияextracted three times with methylene chloride
4. 4
   ПромывкаThe combined organic layers were washed with brine
5. 5
   Сушкаdried over sodium sulfate
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated
8. 8
   ДругоеThe residue was purified by flash chromatography
9. 9
   Промывкаeluting with 20% ethyl acetate in hexanes

Методика

To a solution of tert-butyl 1-(1-hydroxyprop-1-yl)-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate (0.050 g, 0.16 mmol) from Step E in acetone (2 mL) at 0° C. was added 2.6M Jones reagent (0.122 mL, 0.32 mmol). The reaction was stirred at room temperature for 10 min and was then quenched with isopropanol. The mixture was diluted with water and extracted three times with methylene chloride. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography eluting with 20% ethyl acetate in hexanes to afford the title compound (0.033 g).

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