Methyl iodide → HCID 178486046, compound

Participants

Reaction Steps

To a suspension of NaH (1.0 g, 41 mmol, 2.5 equiv) in DMF (30 mL) at −10° C. was added cis-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexanecarboxylic acid (4.0 g, 16 mmol, 1.0 equiv). The reaction mixture was allowed to warm to room temperature and then was stirred for 1 h. The mixture was again cooled to −10° C., and MeI (25 g, 260 mmol, 16 equiv) was added dropwise. The cold bath was removed, and the reaction mixture was stirred for 3 h at room temperature. The mixture was poured onto ice, and then NaOH (1.5 g) was added to hydrolyze any undesired methyl ester that formed. This solution was stirred for another 4 hours. The aqueous layer was washed with ethyl acetate and concentrated under reduced pressure to remove the DMF. The resulting residue was diluted with water, and the pH was adjusted to ˜3-4. The desired product precipitated as a white solid which was collected by filtration (2.5 g).

Provenance & Evidence