3-[(3-fluoro-6-methylphenanthridin-5(6H)-yl)carbonyl]phenol → 3-{[(6R)-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 first peak were combined and concentrated in vacuo, to provide one peak (99.9%) with a retention time of 2.708 minutes was isolated as a white solid (270 mg, 82% based upon a 1:1 ratio of enantiomers with a theoretical maximum amount of 330 mg). [α]D25 =−545° (c=0.0105 g/mL, CHCl3); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21 (d, J=6.98 Hz, 3 H) 5.66 (q, J=6.38 Hz, 1 H) 6.69 (d, J=7.24 Hz, 2 H) 6.72 (s, 1 H) 6.83 (ddd, J=8.15, 2.46, 0.78 Hz, 1 H) 7.09 (td, J=8.67, 2.59 Hz, 1 H) 7.16 (t, J=7.89 Hz, 1 H) 7.37 (m, 2 H) 7.44 (td, 1 H) 7.96 (d, J=7.76 Hz, 1 H) 8.00 (dd, J=8.79, 6.47 Hz, 1 H) 9.66 (s, 1 H) MS (ESI) 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+), 334.12345.

Provenance & Evidence