Sodium borohydride → Benzenamine, 4-(5,5-dimethyl-4-(4-pyridinyl)-2-pyrrolidinyl)-, cis-(+-)-

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Reaction Steps

0.55 G. of sodium borohydride are added to a solution of 1.85 g. of 4-[2-(p-aminophenyl)-5,5-dimethyl-1-pyrrolin-4-yl]-pyridine in 18.5 ml. of methanol and the mixture is stirred at room temperature for 2 hours. Then, an additional 0.55 g. of sodium borohydride are added and the reaction mixture is left to stand at room temperature overnight. The reaction mixture is then evaporated under reduced pressure and the resulting residue taken up in water and extracted three times with methylene chloride. The organic phase is dried over sodium sulfate and evaporated under reduced pressure. The resulting crude product is chromatographed on silica gel with chloroform/methanol/ethyl acetate/ammonia (60:10:2:1). The material obtained, after crystallization with ether, yields 4-[cis-5-(p-aminophenyl)-2,2-dimethyl-3-pyrrolidinyl]-pyridine of melting point 119°-120° C. The trihydrochloride, recrystallized from methanol/ether, has a melting point of 223°-226° C.

Provenance & Evidence