Chloroform → 5-chloro-N-[trans-3-(4-methanesulfonyl-phenyl)-2,2-dimethyl-cyclopropyl]-2-methoxy-benzamide

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Reaction Steps

Chlorosulfonic acid (0.17 mL) was added at 0° C. to a solution of 5-chloro-N-(Trans-2,2-dimethyl-3-phenyl-cyclopropyl)-2-methoxy-benzamide (165 mg, 0.5 mmol) in chloroform (8 mL), and the resulting mixture was stirred at room temperature for 1.5 hour. The reaction was then quenched by addition of ice and the resulting mixture was extracted with diethyl ether. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran (10 mL) and cooled to 0° C. Hydrazine (0.05 mL) was added and the resulting mixture was stirred for 18 hours. The reaction mixture was evaporated under reduced pressure and the residue was dissolved in ethanol (15 mL). Sodium acetate (205 mg) and methyl iodide (355 mg) were added and the resulting mixture was heated to reflux for 18 hours. The reaction mixture was then evaporated under reduced pressure and the residue was partitioned between brine and diethyl ether. The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was absorbed onto silica gel and purified by flash chromatography (EtOAc/hexane, 0-25%) to give 37 mg of 5-chloro-N-[trans-3-(4-methanesulfonyl-phenyl)-2,2-dimethyl-cyclopropyl]-2-methoxy-benzamide colorless viscous oil.

Provenance & Evidence