Ammonium Chloride → [10-(5-Fluoro-3-pyridyl)-8-hydroxy-11-oxa-3-azaspiro[5.5]undec-9-en-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone

Participants

Reaction Steps

To a solution of 10-(5-fluoro-3-pyridyl)-3-(4-isopropoxy-3-methyl-benzoyl)-11-oxa-3-azaspiro[5.5]undec-9-en-8-one (273 mg, 0.62 mmol) in methanol (7.8 mL) was slowly added sodium borohydride (25 mg, 0.65 mmol) The reaction mixture was allowed to stir for 30 minutes. A solution of saturated aqueous ammonium chloride (50 mL) was added. After brief stirring, the mixture was concentrated to half volume and was extracted with dichloromethane (3×75 mL). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified on silica gel utilizing a gradient of 60-100% ethyl acetate in hexanes to yield [10-(5-fluoro-3-pyridyl)-8-hydroxy-11-oxa-3-azaspiro[5.5]undec-9-en-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (256 mg) as a colorless oil. ESI-MS m/z calc. 440.2, found 441.3 (M+1)+; Retention time: 1.73 minutes (3 min run).

Provenance & Evidence