Réaction #674312

Équation de réaction

tert-butyl 3-hydroxypiperidine-1-carboxylate

Dess-Martin periodinane

→

tert-butyl 3-oxopiperidine-1-carboxylate

Rendement 86.5%

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   Températureto warm to room temperature slowly
2. 2
   workup.STIRRINGThe solution was stirred at room temperature for 18 hrs
3. 3
   AutreThe white solid was removed by filtration
4. 4
   Lavageeluted with EtOAc (100 mL)
5. 5
   LavageThe combined organic phase was washed with saturated solution of NaHCO3 (50 mL)
6. 6
   Séchagedried over anhydrous Na2SO4
7. 7
   Concentrationconcentrated

Mode opératoire

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.

Source