Cornforth reagent → Methyl(4-oxobutyl)carbamate

HRID 654172Notes

Reaction equation

HRID 654172 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[OH:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27](C)[C:28](=[O:34])[O:29][C:30](C)(C)C>ClCCl>[CH3:30][O:29][C:28](=[O:34])[NH:27][CH2:26][CH2:25][CH2:24][CH:23]=[O:22]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 14854943tert-Butyl (4-hydroxybutyl)(methyl)carbamate

Product 1

HCID 19888448Methyl(4-oxobutyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred and cooled (<10° C.) solution of 150 parts of pyridinium dichromate in 1300 parts of dichloromethane was added dropwise a solution of 50 parts of (1,1-dimethylethyl) (4-hydroxybutyl)methylcarbamate in 91 parts of dichloromethane. Upon complete addition, stirring was continued for 3 hours in the presence of 112 parts of molecular sieves of 4A at room temperature. The reaction mixture was filtered over magnesium sulfate, washed with 1,1'-oxydisethane and the filtreate was evaporated. The residue was purified by column chromatography over silica gel using dichloromethane as eluent. The pure fractions were collected and the eluent was evaporated. The residue was taken up in methylbenzene and the whole was evaporated again, yielding 3.5 parts (6.9%) of (1,1-dimethylethyl) (methyl(4-oxobutyl)carbamate as a residue (interm. 7).

Workup

  1. additionUpon complete addition
  2. stirringstirring
  3. filtrationThe reaction mixture was filtered over magnesium sulfate
  4. washwashed with 1,1'-oxydisethane
  5. customthe filtreate was evaporated
  6. customThe residue was purified by column chromatography over silica gel
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customthe whole was evaporated again

Sources & evidence

ORD record
ord-4d2f3908518a4ddab1cf8f375773f0ed
Source dataset
uspto-grants-1992_07
Patent number
US05130312

Reaction notes

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