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Dolbier HW Solutions 544

Dolbier HW Solutions 544 - 638 AMINES conguration at the...

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con f guration at the alcohol carbon. Conversion of the alcohol to its p -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, and the 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 substitution reaction 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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