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Dimethyl Sulfoxide → 1-Boc-4-methylpiperidine-4-carboxamide

HRID 1408328
Notes
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Reaction equation

HRID 1408328 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

HCID 533937931-Boc-4-methylpiperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

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-dbf3d31d312b400d9448e9a823d1da39
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921350B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes