Reaktion #674312

Reaktionsgleichung

tert-butyl 3-hydroxypiperidine-1-carboxylate

Dess-Martin periodinane

→

tert-butyl 3-oxopiperidine-1-carboxylate

Ausbeute 86.5%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature slowly
2. 2
   workup.STIRRINGThe solution was stirred at room temperature for 18 hrs
3. 3
   SonstigeThe white solid was removed by filtration
4. 4
   Wascheneluted with EtOAc (100 mL)
5. 5
   WaschenThe combined organic phase was washed with saturated solution of NaHCO3 (50 mL)
6. 6
   Trocknendried over anhydrous Na2SO4
7. 7
   Einengenconcentrated

Vorschrift

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.

Quelle