Sodium borohydride → N-(5-Hydroxymethyl-pyridin-2-yl)-2,2-dimethyl-propionamide

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Reaction Steps

N-(5-formyl-pyridin-2-yl)-2,2-dimethyl-propionamide (6.96 g) under an argon atmosphere in MeOH (120 mL) was cooled to 0° C. and then treated portion wise with sodium borohydride (1.289 g). The cooling bath was removed, stirring was continued for 30 minutes and the reaction mixture was partitioned between half-saturated aqueous NH4Cl and AcOEt. The layers were separated, the organic layer dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (heptane/AcOEt 1:1 to 1:2) to give N-(5-hydroxymethyl-pyridin-2-yl)-2,2-dimethyl-propionamide (3.4 g) as a crystalline white solid. MS (ESI): 209.2 (MH+).

Provenance & Evidence