4-(5-(4-(2,5-Bis(4-nitrophenyl)pyrrolidin-1-yl)phenyl)pyridin-2-yl)morpholine → 4,4'-(1-(4-(6-Morpholinopyridin-3-yl)phenyl)pyrrolidine-2,5-diyl)dianiline

Participants

Reaction Conditions

Reaction Steps

Charged a 100-mL round bottom flask with the product of Example 108A (174.7 mg, 0.317 mmol), partially dissolved in THF (12.50 mL) and absolute EtOH (2.50 mL), evacuated on house vacuum and filled flask with nitrogen, then added platinum (IV) oxide (14.38 mg, 0.063 mmol), evacuated flask on house vacuum and filled with hydrogen from a balloon, repeated evacuation/filling cycle 3 times, and stirred heterogeneous reaction mixture vigorously under hydrogen (1 atm). After 2 hr, charged reaction with additional platinum (IV) oxide (14.38 mg, 0.063 mmol) and continued to vigorously stir under hydrogen at 25° C. After 5 hr, added additional platinum (IV) oxide (14.38 mg, 0.063 mmol). The reaction mixture was then vacuum filtered through a bed of Celite 545 in a Büchner funnel, the filter pad was washed with CHCl3 (100 mL) and hot CHCl3 (2×50 mL), and the filtrate concentrated by rotary evaporation to give the title compound as a yellow solid (101 mg, 65%) as a mixture of stereoisomers. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.71-1.87 (m, 2H), 2.24-2.31 (m, 1H), 3.37-3.45 (m, 4H), 3.64-3.74 (m, 4H), 4.57 (t, J=4.99 Hz, 2H), 4.95 (s, 4H), 6.42-6.53 (m, 3H), 6.57 (d, J=8.35 Hz, 4H), 6.76-6.89 (m, 2H), 7.15 (d, J=8.35 Hz, 4H), 7.26 (d, J=8.78 Hz, 2H), 7.68 (dd, J=8.84, 2.44 Hz, 1H), 8.29 (d, J=2.39 Hz, 1H); MS (ESI+) m/z 492 (M+H)+.

Provenance & Evidence