Sodium cyanoborohydride → HCID 59442007, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[3-(methyloxy)-4-nitrophenyl]-1-(2-propen-1-yl)pyridinium bromide (28.2 g, 80.0 mmol) in MeOH (200 mL) was added NaBH3CN (21.1 g, 320.0 mmol). The reaction was heated to 65° C. and stirred for 72 h. The cooled solution was concentrated to remove MeOH, and to the residue was added saturated aq. NaHCO3 (100 mL). After extraction with Ethyl acetate (2×100 mL), concentration, and drying (Na2SO4), purification by silica chromatography afforded 5-[3-(methyloxy)-4-nitrophenyl]-1-(2-propen-1-yl)-1,2,3,6-tetrahydropyridine (11.0 g, 50%). ESIMS (M+H)+=275.

Provenance & Evidence