Reaction #674312

Reaction equation

tert-butyl 3-hydroxypiperidine-1-carboxylate

Dess-Martin periodinane

→

tert-butyl 3-oxopiperidine-1-carboxylate

Yield 86.5%

Solvents

DCM

Conditions

Workup

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

Procedure

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