Methyl iodide → HCID 178501226, compound

Participants

Reaction Steps

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).

Provenance & Evidence