Dimethyl Sulfoxide → tert-Butyl 4-carbamoyl-4-methylpiperidine-1-carboxylate

HRID 871900Notes

Reaction equation

HRID 871900 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]#[N:16])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CS(C)=[O:19].[OH-].[Na+].OO>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15](=[O:19])[NH2:16])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 46835621tert-Butyl 4-cyano-4-methylpiperidine-1-carboxylate

Product 1

HCID 53393793tert-Butyl 4-carbamoyl-4-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-cyano-4-methyl-piperidine-1-carboxylic acid tert-butyl ester (2.24 g, 10 mmol) in methanol (25 mL) was added DMSO (1 mL), aqueous 1N NaOH (12 mL, 12 mmol) and H2O2 (4 mL) at room temperature. The mixture was heated at 50° C. for 3 hours. After cooling to room temperature, the mixture was partitioned between EtOAc and H2O. The organic layer was washed successively with H2O and brine. After drying (Na2SO4), the solvent was removed to afford the desired product.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between EtOAc and H2O
  3. washThe organic layer was washed successively with H2O and brine
  4. dry with materialAfter drying (Na2SO4)
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-9636db40fb2740e0a0b9776e38af21a9
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

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