Sodium borohydride → 4-(3-Methoxy-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridine

Participants

Reaction Steps

To 4-[3-(methyloxy)-4-nitrophenyl]-1-propylpyridinium iodide (5.7 g, 14.24 mmol) in 75 mL of MeOH at 0° C. was added, NaBH4 (1.62 g, 42.73 mmol) over 1 h. The mixture was allowed to come to rt over 2 h. The solvent was reduced to approximately 20 mL and then diluted with EtOAc, washed with conc. NaHCO3, dried (Na2SO4), filtered, rotovaped down, and purified by flash chromatography to give the title compound of step C (3.33 g, 12.05 mmol, 85%). 1H NMR (400 MHz, CDCl3) δ ppm 7.84 (d, J=8.42 Hz, 1H), 7.02 (s, 1H), 6.99-7.02 (m, 1H), 6.19 (ddd, J=3.43, 1.92, 1.79 Hz, 1H), 3.95 (s, 3H), 3.20 (q, J=2.81 Hz, 2H), 2.72 (t, J=5.68 Hz, 2H), 2.54-2.60 (m, 2H), 2.41-2.48 (m, 2H), 1.54-1.64 (m, 2H), 0.94 (t, J=7.42 Hz, 3H).

Provenance & Evidence