Sodium borohydride → HCID 53712702, compound

Participants

Reaction Conditions

Reaction Steps

α-(Methoxyimino)-α-(1-methylpyridinium-3-yl)acetonitrile iodide (D6) (0.3 g, 0.001 mol) was dissolved in methanol (10 ml) and cooled to 0° C. Sodium borohydride (0.114 g, 0.003 mol) was added in three equal portions at 15 minute intervals. The mixture was allowed to warm to room temperature over 1 h and then evaporated to dryness. The residue was partitioned between saturated aqueous potassium carbonate solution (50 ml) and chloroform (3×75 ml). The organic layers were separated and dried (Na2SO4) then filtered and evaporated to dryness. The residue was subjected to column chromatography on silica gel eluting with 0-1% methanol/chloroform. This gave the title compound (D7) as an oil (0.04 g, 23%). A portion of this material was converted to the oxalate salt and crystallised from ethanol/diethyl ether to give a white crystalline solid m.p. 157°-158° C.

Provenance & Evidence