Water → Tert-butyl (2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

Tert-butyl (2S)-2-{(3-fluoro-4-methylphenyl)[(1H-imidazol-1-yl carbonothioyl)oxy]methyl}pyrrolidine-1-carboxylate (0.83 g, 1.98 mmol), which had been obtained in Example 1 (1c), and a solution of tributyl tin hydride (1.73 g, 5.94 mmol) and 2,2′-azobis(isobutyronitrile) (0.07 g, 0.40 mmol) in toluene (4 mL) were stirred with heating under reflux for 6 hours. The reaction solution was cooled to room temperature. Water (20 mL) was added to the reaction solution, which was then extracted with ethyl acetate (20 mL×3). After that, the organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to give the title compound as a colorless oily substance (0.33 g, yield 57%).

Provenance & Evidence