confguration at the alcohol carbon. Conversion of the alcohol to itsp-toluenesulfonate ester en-sures that the leaving group is introduced with exactly the same stereochemistry as the alcohol.Once the leaving group has been introduced with the proper stereochemistry, it can be dis-placed by a nitrogen nucleophile suitable for subsequent conversion to an amine.(As actually reported, the azide was reduced by hydrogenation over a palladium catalyst, andthe amine was isolated as its hydrochloride salt in 66% yield.)(d)Recognition that the primary amine is derivable from the corresponding nitrile by reduction,and that the necessary tertiary amine function can be introduced by a nucleophilic substitutionreaction between the two given starting materials suggests the following synthesis.Alkylation of N-methylbenzylamine with 4-bromobutanenitrile has been achieved in 92%yield in the presence of potassium carbonate as a weak base to neutralize the hydrogen bro-mide produced. The nitrile may be reduced with lithium aluminum hydride, as shown in the
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