m-Chloroperbenzoic acid → (8R,9S,13S,14S,17R)-4-Fluoro-17-hydroxy-13-methyl-17-[(1-oxidopyridin-1-ium-4-yl)methyl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of EM-5855 (86 mg, 0.22 mmol) in anhydrous dichloromethane (5 mL) at 0° C. was added 3-chloroperoxybenzoic acid (54 mg, 0.22 mmol). The mixture was stirred for 16 h at 22° C. and evaporated to dryness. The crude compound was purified by flash chromatography (silica gel, 0-10% methanol in chloroform) to give 67 mg (75%) of EM-5854. 1H NMR (400 MHz, CDCl3) δ: 0.94 (s, 3H, Me), 2.57 (d, Jgem=13.5 Hz, 1H, —CH2-Pyr), 2.68 (m, 1H, H-6), 2.93 (d, Jgem=13.3 Hz, 2H, —CH2-Pyr, H-6), 7.17 (d, J=8.3 Hz, 1H, Ar), 7.27 (d, J=6.0 Hz, 2H, Pyr), 7.36 (t, J=7.7 Hz., 1H, Ar), 8.01 (d, J=6.8 Hz, 2H, Pyr).

Provenance & Evidence