Methyl iodide → HCID 59625403, compound

HRID 2192832Notes

Reaction equation

HRID 2192832 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:29][CH:30]([CH3:32])[CH3:31])[C@@H:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15][C@H:14]([C:25]([O:27][CH3:28])=[O:26])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH3:34].[H-].[Na+]>CN(C=O)C.[Cl-].[NH4+]>[CH2:1]([O:8][C:9]([N:11]([CH2:29][CH:30]([CH3:32])[CH3:31])[C@@H:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:15][C:14]([CH3:34])([C:25]([O:27][CH3:28])=[O:26])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59625536HCID 59625536, compound

Product 1

HCID 59625403HCID 59625403, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

1-tert-Butyl 3-methyl (3R,5S)-5-{[(benzyloxy)carbonyl](2-methylpropyl)amino}piperidine-1,3-dicarboxylate (430 mg) and iodomethane (90 μl) were dissolved in DMF (5 ml), sodium hydride (50% contained, 70 mg) was added under ice-cooling, and the mixture was stirred at room temperature for 10 hr. The reaction mixture was diluted with saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object compound (500 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d49f71ab6e0144c0967422ed643c57d5
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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