Sodium borohydride → HCID 17857898, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-benzyl-5-(methoxycarbonyl)-2-methylpyridinium bromide (3.2 g, 9.9 mmol) in methanol (50 ml) was added at −70° C. a solution of sodium borohydride (0.75 g, 20 mmol) in water (10 ml). The mixture was raised to 0° C. and stirred for 20 minutes. The reaction mixture was added to ethyl acetate/brine and the mixture was separated with a separating funnel. The aqueous layer was extracted twice with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and the solvent was removed in vacuo. The residue (2.34 g) was purified with silica gel (60 g) chromatography (hexane/ethyl acetate=4/1) to give methyl 1-benzyl-6-methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylate (2.05 g, 84%).

Provenance & Evidence