cis-4-(tert-Butoxycarbonylamino)cyclohexanol → tert-butyl N-(4-oxocyclohexyl)carbamate

HRID 69577Notes

Reaction equation

HRID 69577 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[O:14]=[C:11]1[CH2:10][CH2:9][CH:8]([NH:7][C:6](=[O:15])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 1514287cis-4-(tert-Butoxycarbonylamino)cyclohexanolHCID 178418287HCID 178418287, compound

Product 1

HCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateYield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was re-dissolved in EtOAc/n-hexane (1000 mL)
  3. filtrationfiltered through celite
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customEvaporation of the solvents

Sources & evidence

ORD record
ord-2cd8458fbe45458eb73dfd8fccddb277
Source dataset
uspto-grants-2014_09
Patent number
US08822507B2

Reaction notes

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