4-[(3-fluoro-6-methylphenanthridin-5(6H)-yl)carbonyl]phenol → 4-{[(6S)-3-fluoro-6-methylphenanthridin-5(6H)-yl]carbonyl}phenol

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Reaction Steps

The enantiomers of 4-[(3-fluoro-6-methylphenanthridin-5(6H)-yl)carbonyl]phenol (720 mg, 2.16 mmol) were separated by automated, on-column solvent change, preparative, normal phase, chiral chromatography on a Chiralpak AD (20 mm×250 mm) column eluting with 35% hexane in ethanol at a flow rate of 15 mL/min with. The fractions containing the second peak were combined and concentrated in vacuo, to provide one peak (99.8%) with a retention time of 8.095 minutes was isolated as a white solid (345 mg, 96% based upon a 1:1 ratio of enantiomers with a theoretical maximum amount of 360 mg). mp 236.6-237.8° C.; [α]D25=+581° (c=0.0107 g/mL, CHCl3); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21 (d, J=6.73 Hz, 3 H) 5.68 (q, J=6.73 Hz, 1 H) 6.56 (dd, J=10.60, 2.59 Hz, 1 H) 6.70 (d, J=8.79 Hz, 2 H) 7.06 (td, J=8.54, 2.59 Hz, 1 H) 7.16 (m, 2 H) 7.35 (m, 1 H) 7.42 (m, 2 H) 7.98 (td, J=8.79, 6.98 Hz, 2 H) 10.04 (s, 1H) MS (ESI) m/z 334 ([M+H]+); MS (ESI) m/z 332 ([M−H]−).

Provenance & Evidence