Dichloromethane → Benzyl (4-oxocyclohexyl)carbamate

HRID 1457602Notes

Reaction equation

HRID 1457602 reaction equation
ClCCl.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:15]([O:22][C:23]([NH:25][C@H:26]1[CH2:31][CH2:30][C@H:29]([OH:32])[CH2:28][CH2:27]1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)C>[CH2:15]([O:22][C:23]([NH:25][CH:26]1[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]1)=[O:24])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 178418287HCID 178418287, compoundHCID 178523817HCID 178523817, compound

Product 1

HCID 14615292Benzyl (4-oxocyclohexyl)carbamateYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 1000 ml of dichloromethane suspension containing 25.9 g of pyridinium chlorochromate (PCC) was added dropwise under ice-cooling a mixture of 15 g of N-benzyloxycarbonyl-trans-4-aminocyclohexanol and 1000 ml of dichloromethane. The resulting mixture was stirred at room temperature for 4 hours. Then, diethyl ether was added to the reaction mixture and insoluble materials were removed by filtration from the mixture. The filtrate was condensed and the residue was purified by silica gel column chromatography (solvent; chloroform:methanol=10:1) to give 10.562 g of N-benzyloxycarbonyl-4-aminocyclohexanone (yield: 71%, melting point: 65°-69° C.).

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. customwere removed by filtration from the mixture
  4. customcondensed
  5. customthe residue was purified by silica gel column chromatography (solvent; chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-7ef58ee764ce4bb3bc013adb256b369c
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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