Hydrogen Bromide → HCID 58452638, compound

Participants

Reaction Conditions

Reaction Steps

48% hydrobromic acid (1 mL) was added to a solution of (5R)-5-[2-(4-tert-butylphenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethyl]pyrrolidin-2-one (100 mg) in 1,4-dioxane (2 mL), and the mixture was stirred at room temperature for 30 minutes and at 65° C. for 30 minutes. The reaction solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by preparative TLC (chloroform:methanol=10:1) to give 6-{1-(4-tert-butylphenyl)-2-[(2R)-5-oxopyrrolidin-2-yl]ethyl}-3-chloropyridin-2(1H)-one, which was separated by preparative HPLC (Inertsil ODS-3 (20 mm i.d.×250 mm L, GL Sciences Inc.), 40° C., flow rate: 10 mL/min, acetonitrile:water=40:60). The fraction containing a single diastereomer eluted with a retention time of 43 minutes was concentrated to give the title compound as a white solid (18 mg, 19%) (Example 4-69).

Provenance & Evidence