反应详情

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).

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)