Water → (S)-8-Fluoro-5-(4-methoxy-benzenesulfonyl)-6-methyl-5,6-dihydrophenanthridine

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of N-[(1S)-1-(2′,4-difluoro-1,1′-biphenyl-2-yl)ethyl]-4-methoxybenzenesulfonamide (1.7 g, 4.2 mmol) and potassium carbonate (1.16 g, 8.4 mmol) in N,N-dimethylformamide (25 mL) was heated at 100° C., and the reaction progress was monitored by LCMS. After 96 hours, water (300 mL) was added with stirring. A precipitate was filtered and washed with copious amounts of water. The product was purified by preparative liquid chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g), eluting with a gradient of 30%-50% methyl tert-butylether in hexane, to afford a purified solid. Recrystallization of the solid afforded (6S)-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine* (1.4 g, 87%, >99.9% ee), m.p. 196.8-198° C.;

Provenance & Evidence