Methyl iodide → HCID 178501226, compound

HRID 409494Notes

Reaction equation

HRID 409494 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][CH2:6]1)=[O:4].[H-].[Na+].I[CH3:22].[Cl-].[NH4+]>CN(C)C=O>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH3:22])[CH2:9][CH2:10]1)=[O:4]

Participants

6

Reactant 4

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

Product 1

HCID 178501226HCID 178501226, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of trans-4-(tert-butoxycarbonylamino)cyclohexane carboxylic acid methyl ester (5 mmol, 1.3 g) in dimethylformamide (15 mL) is cooled to 0° C. and treated with of sodium hydride (60% in oil, 6 mmol, 240 mg) over 30 minutes. The mixture is stirred at room temperature for 1 hour, then cooled to 0° C. and treated with iodomethane (6 mmol, 0.38 mL). After stirring overnight at room temperature, the mixture is poured into a saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined organic phase is washed with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue is purified by column chromatography on silica gel (eluent: n-hexane-ethyl acetate 10:1) to obtain 1.3 g (96%) of trans-4-[(tert-Butoxycarbonyl)(methyl)amino]cyclohexane carboxylic acid methyl ester as colorless oil. ESI-MS m/z: 272 [M+1]+, Retention time 3.57 min (condition B).

Workup

  1. temperaturecooled to 0° C.
  2. stirringAfter stirring overnight at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phase is washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue is purified by column chromatography on silica gel (eluent: n-hexane-ethyl acetate 10:1)

Sources & evidence

ORD record
ord-0d59e9bc6d404d4cbc92841930b0e73d
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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