Methyl iodide → HCID 178501226, compound

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Reaction Steps

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).

Provenance & Evidence