Benzyl (3-hydroxycyclohexyl)carbamate → Benzyl (3-oxocyclohexyl)carbamate

HRID 1013813Notes

Reaction equation

HRID 1013813 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([OH:17])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[CH2:1]([O:8][C:9](=[O:18])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14476840Benzyl (3-hydroxycyclohexyl)carbamateHCID 178418287HCID 178418287, compound

Product 1

HCID 10171453Benzyl (3-oxocyclohexyl)carbamateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a solution of (3-hydroxy-cyclohexyl)-carbamic acid benzyl ester (15.5 g, 62.24) in dichloromethane (300 mL) with PCC (16.73 g, 77.81 mmol) and stir the mixture at room temperature for 12 hours. Filter the reaction mixture through celite. Remove the solvent in vacuo. Purify the residue on silica gel column using 25% to 50% ethyl acetate in hexanes gradient to afford 12.6 g (82%) of the title compound. MS (m/z): 248 (M+).

Workup

  1. filtrationFilter the reaction mixture through celite
  2. customRemove the solvent in vacuo
  3. customPurify the residue on silica gel column

Sources & evidence

ORD record
ord-465aeaafce25464da4ee1600c86b5d31
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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