Ethyl Acetate → HCID 57467658, compound

Participants

Reaction Steps

The mixture of methyl 4-(5-fluoro-2-methoxypyridin-4-yl)-3-(1-formylcyclopentyl)benzoate (0.13 g, 0.36 mmol) in DCM (6.0 mL) and MeOH (1.5 mL) was reacted with ozone gas at −78° C. for 10 minutes. The excess ozone was removed by flushing with nitrogen, and dimethylsulfide (0.3 mL) was added. The resulting reaction mixture was stirred at room temperature for 30 minutes. Sodium borohydride (0.13 mL, 3.6 mmol) was added to the reaction mixture, and the reaction was stirred at room temperature overnight. EtOAc (50 mL) was added, and the organic layer was washed with brine (20×2 mL) and dried over Na2SO4. After filtration, the solvent was removed. The product thus obtained was used in the next step without further purification. MS ESI (pos.) m/e: 360.2 (M+H)+.

Provenance & Evidence