4-[(3-fluoro-6-methylphenanthridin-5(6H)-yl)carbonyl]benzene-1,3-diol → 4-{[(6S)-3-fluoro-6-methylphenanthridin-5(6H)-yl]carbonyl}benzene-1,3-diol

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Reaction Steps

The enantiomers of 4-[(3-fluoro-6-methylphenanthridin-5(6H)-yl)carbonyl]benzene-1,3-diol (800 mg, 2.29 mmol) were separated by automated, preparative, normal phase, chiral chromatography on a Chiralpak AS (20 mm×250 mm) column eluting with 15% isopropyl alcohol in hexane at a flow rate of 20 mL/min with. The fractions containing the second peak were combined and concentrated in vacuo, to provide one peak (99.3%) with a retention time of 9.345 minutes was isolated as a white solid (220 mg, 55% based upon a 1:1 ratio of enantiomers with a theoretical maximum amount of 400 mg). mp 182-184° C.; [α]D25=+618° (c=0.0101 g/mL, CHCl3); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.16 (d, J=6.73 Hz, 3 H) 5.65 (d, J=6.73 Hz, 1 H) 6.16 (d, J=1.81 Hz, 1 H) 6.22 (dd, J=8.41, 2.20 Hz, 1 H) 6.75 (d, J=10.35 Hz, 1 H) 6.98 (d, J=8.28 Hz, 1 H) 7.04 (td, J=8.60, 2.72 Hz, 1 H) 7.33 (m, 2 H) 7.39 (ddd, J=7.70, 6.79, 2.07 Hz, 1 H) 7.90 (d, J=7.50 Hz, 1 H) 7.94 (dd, J=8.79, 6.47 Hz, 1 H) 9.62 (s, 1 H) 9.70 (s, 1 H) MS (ESI) m/z 350 ([M+H]+); MS (ESI) m/z 348 ([M−H]−); HRMS: calcd for C21H16FNO3, 349.1114 (M), 350.1187 ([M+H]+); found (ESI+), 350.11817.

Provenance & Evidence