Hydrogen Peroxide → (3aR,5R,6aR)-5-methyl-1-(4'-(6-oxopyridazin-1(6H)-yl)biphenyl-4-yl)octahydropyrrolo[3,4-b]pyrrole 5-oxide

Participants

Reaction Conditions

Reaction Steps

A solution of the product from Example 1G (5 g, 13.44 mmol) in DCM (80 mL) and MeOH (40 mL) was treated with hydrogen peroxide (5.2 mL, 30% in H2O, 53.8 mmol). The mixture was heated to 50° C. for 48 hours. The mixture was concentrated under reduced pressure to a smaller volume while still in a solution. The solution was loaded onto an ANALOGIX SuperFlash silica gel column (ANALOGIX is a registered trademark of Analogix Inc. of Burlington, Wis.) and eluted with NH4OH/MeOH/DCM (1/10/90) to obtain the faster moving component (comparing with Example 1I) as the title product. 1H NMR (300 MHz, DMSO) δ ppm 8.06 (m, 1H), 7.69 (d, J=9 Hz, 2 H), 7.57 (d, J=9 Hz, 4 H), 7.50 (d, J=6 Hz, 1 H), 7.08 (dd, dd, J=9, 4.0 Hz, 1 H), 6.70 (d, J=9 Hz, 2 H), 4.72 (d, J=6 Hz, 1 H), 3.75-3.82 (m, 1 H), 3.52-3.59 (m, 2 H), 3.36-3.45 (m, 3 H), 3.15-3.21 (m, 1 H), 3.14 (s, 3 H), 2.05-2.12 (m, 1 H), 1.80-1.86 (m, 1 H); MS (DCI,) M+=388.

Provenance & Evidence