Methyl iodide → HCID 178501226, compound

HRID 491828Notes

Reaction equation

HRID 491828 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:21]I.[Cl-].[NH4+]>CN(C)C=O.CO>[C:1]([O:5][C:6]([N:8]([C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:13][CH2:14]1)[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 178501239HCID 178501239, compound

Product 1

HCID 178501226HCID 178501226, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl trans-4-(t-butoxycarbonylamino)-cyclohexanecarboxylate (30.00 g) is dissolved in N,N-dimethylformamide (150 ml) and thereto is added 60% sodium hydride in oil (5.60 g) under ice-cooling. After stirring for 0.5 hours under cooling, to the reaction solution are added methyl iodide (14.5 ml) and methanol (0.15 ml) successively, and the reaction solution is warmed to room temperature and stirred for 4 hours. Under ice-cooling, to the reaction solution are poured saturated ammonium chloride and ice-water, and the mixture is extracted with ethyl acetate. The organic layer is washed with water and saturated brine successively, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1, followed by 7/1) to give methyl trans-4-(N-t-butoxycarbonyl-N-methylamino)cyclohexanecarboxylate (26.33 g).

Workup

  1. temperaturecooling
  2. temperatureunder cooling, to the reaction solution
  3. stirringstirred for 4 hours
  4. temperatureUnder ice-cooling, to the reaction solution
  5. extractionthe mixture is extracted with ethyl acetate
  6. washThe organic layer is washed with water and saturated brine successively
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto remove the solvent under reduced pressure
  10. customThe resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1, followed by 7/1)

Sources & evidence

ORD record
ord-3b95a011d79c497594022a3272bd12f6
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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