Methyl iodide → HCID 69862800, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% w/w in mineral oil, 20 mg, 0.52 mmol) was added to a solution of 4-benzyl-5-(2-tert-butylcarbamoyl-5-hydroxy-cyclohexylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (200 mg, 0.40 mmol) in dry N,N-dimethylformamid (4 ml) stirred at 0° C. under nitrogen. The resulting mixture was stirred at 0° C. until gas evolution had ceased. Methyl iodide (40 μl, 0.6 mmol) was then added, and the solution was allowed to warm to room temperature and stirred for 20 hours. After removal of the volatiles in vacuo, the crude product was dissolved in ethyl acetate, washed twice with water, dried (anhydrous magnesium sulfate) and concentrated in vacuo. Purification by flash chromatography on silica gel provided 4-benzyl-5-(2-tert-butylcarbamoyl-5-methoxy-cyclohexylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (125 mg, 96%).

Provenance & Evidence