Trimethylsilyl iodide → HCID 57650311, compound

Participants

Reaction Steps

To a solution of (R)-benzyl 2-(4-(4-chlorobenzyl)-3-methylisoxazol-5-yl)pyrrolidine-1-carboxylate (220 mg, 0.54 mmol) in dichloromethane (20 mL) at 0° C. was added iodotrimethylsilane (110 μL, 0.8 mmol). The reaction mixture was allowed to warm to room temperature, stirred for 3 h, concentrated in vacuo and diluted with ether (30 mL). The organic layer was extracted with 1M HCl (2×50 mL). The aqueous layer was basified with 6 M NaOH and extracted with dichloromethane (3×50 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford (R)-4-(4-chlorobenzyl)-3-methyl-5-(pyrrolidin-2-yl)isoxazole (110 mg, 74%). LCMS: calculated: 276, found (MH+): 277.

Provenance & Evidence