Water → HCID 66701322, compound

Participants

Reaction Steps

Under argon and at 0° C., 4.6 ml of a boron tribromide solution (1 molar in dichloromethane, 4.6 mmol, 2 eq.) were added to a solution of 890 mg (2.3 mmol) of 4-{[3-(4-ethylphenyl)-5-methoxypiperidin-1-yl]carbonyl}morpholine in 22 ml of dichloromethane. The reaction mixture was stirred at RT for 2 h, then poured onto ice, neutralized with solid sodium bicarbonate and, after addition of water and phase separation, extracted three times with dichloromethane. The combined organic phases were dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product was then purified by preparative HPLC (Reprosil C18, water with 0.1% trifluoroacetic acid/acetonitrile gradient). Yield: 314 mg (43% of theory)

Provenance & Evidence