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

Participants

Reaction Steps

The enantiomers of 3-[(3-fluoro-6-methylphenanthridin-5(6H)-yl)carbonyl]phenol (660 mg, 1.98 mmol) were separated by automated, preparative, normal phase, chiral chromatography on a Chiralpak AD (20 mm×250 mm) column eluting with 100% acetonitrile at a flow rate of 20 mL/min with. The fractions containing the second peak were combined and concentrated in vacuo, affording a white solid (270 mg, 82% based upon a 1:1 ratio of enantiomers with a theoretical maximum amount of 330 mg one peak (99.9%) with a retention time of 3.894 minutes; [α]D25=+490° (c=0.0102 g/mL, CHCl3); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21 (d, J=6.98 Hz, 3 H) 5.66 (q, 1 H) 6.69 (d, J=7.50 Hz, 2 H) 6.72 (s, 1 H) 6.83 (ddd, J=8.15, 2.46, 1.03 Hz, 1 H) 7.09 (m, 1 H) 7.16 (t, J=7.89 Hz, 1 H) 7.37 (m, 2 H) 7.44 (m, J=7.37, 7.37, 1.81 Hz, 1 H) 7.96 (d, J=7.50 Hz, 1 H) 8.00 (dd, J=8.79, 6.21 Hz, 1 H) 9.66 (s, 1 H); MS (ES1) m/z 334 ([M+H]+); MS (ESI) m/z 332 ([M−H]−); HRMS: calcd for C21H16FNO2, 333.1165 (M), 334.12379 ([M+H]+); found (ESI+), 334.12344.

Provenance & Evidence