Reaction #710569

Reaction equation

tert-Butyl-4-hydroxycyclohexylcarbamate

PCC

→

title compound

Yield 95.6%

tert-Butyl 4-oxocyclohexylcarbamate

Yield 95.6%

Solvents

DCM

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue was re-dissolved in EtOAc/n-hexane (1000 mL)
3. 3
   Filtrationfiltered through celite
4. 4
   DryingThe organic layer was dried over Na2SO4
5. 5
   OtherEvaporation of the solvents

Procedure

tert-Butyl-4-hydroxycyclohexylcarbamate (17 g) and Celite (17 g) were suspended in dry DCM (100 mL). PCC (25.5 g) was added portion-wise within 10-15 minutes. The reaction was stirred under nitrogen for 2.5 hours. The solvent was removed under reduced pressure and the residue was re-dissolved in EtOAc/n-hexane (1000 mL) and filtered through celite. The organic layer was dried over Na2SO4. Evaporation of the solvents gave the title compound as a colorless solid (16.1 g, quantitative).

Source