Sodium cyanoborohydride → HCID 59441903, compound

Participants

Reaction Steps

To a solution of 3-[4-(methyloxy)-3-nitrophenyl]-1-propylpyridinium iodide (6.10 g, 15.22 mmol) in methanol (100 mL) was added NaBH3CN (9.58 g, 152.06 mmol, Aldrich) and the reaction was allowed to stir overnight at rt. The reaction was quenched with water (50 mL), solvent removed under reduced pressure, aqueous layer extracted with dichloromethane (2×50 mL), organic layers combined, taken to a residue under reduced pressure, and purified by column chromatography on SiO2 to provide 5-[4-(methyloxy)-3-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine (1.89 g, 45% over two steps). ESIMS (M+H)+=277.

Provenance & Evidence