Реакция #674312

Уравнение реакции

tert-butyl 3-hydroxypiperidine-1-carboxylate

Dess-Martin periodinane

→

tert-butyl 3-oxopiperidine-1-carboxylate

Выход 86.5%

Растворители

DCM

Условия реакции

Обработка

1. 1
   Температураto warm to room temperature slowly
2. 2
   workup.STIRRINGThe solution was stirred at room temperature for 18 hrs
3. 3
   ДругоеThe white solid was removed by filtration
4. 4
   Промывкаeluted with EtOAc (100 mL)
5. 5
   ПромывкаThe combined organic phase was washed with saturated solution of NaHCO3 (50 mL)
6. 6
   Сушкаdried over anhydrous Na2SO4
7. 7
   Концентрированиеconcentrated

Методика

To a solution of tert-butyl 3-hydroxypiperidine-1-carboxylate (5 g, 24.84 mmol, 1.0 equiv) in DCM (125 mL) was added Dess-Martin periodinane (11.59 g, 27.33 mmol, 1.1 equiv) at 0° C. in a few portions. The solution was stirred at 0° C. for a while and allowed to warm to room temperature slowly. The solution was stirred at room temperature for 18 hrs. A lot of white solid suspended. The white solid was removed by filtration, eluted with EtOAc (100 mL). The combined organic phase was washed with saturated solution of NaHCO3 (50 mL), dried over anhydrous Na2SO4, concentrated to afford 4.28 g (yield 86%) of tert-butyl 3-oxopiperidine-1-carboxylate as a white solid.

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