Boron tribromide → HCID 9841370, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the title A compound (cis-(-)-2-(ethylthio)-8-(3-hydroxy-1-methyl-4-piperidinyl)-5,7-dimethoxy-4H-1-benzopyran-4-one: 180.5 mg, 0.476 mmol) in 1,2-dichloroethane (3 mL) was added a solution of BBr3 (2.5 mL of 2M solution in 1,2-dichloroethane). The mixture was stirred at 90° C. or 3 hours and cooled to room temperature. It was quenched by MeOH (5 mL) and concentrated. The residue was re-dissolved in MeOH (10 mL) and neutralized by aqueous NaHCO3 solution. The resulting solution was purified by HPLC (YMC OD S-10 30×500 mm; 45% B; flow rate 49 mL/minute; UV 254 nm). Those fractions containing the desired product were pooled, concentrated and lyophilized to afford the title compound (162 mg, 70%) as solid, mp 104° C. [α]D =-19.0° (MeOH, c 0.52).

Provenance & Evidence