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
This is the end of the preview. Sign up
access the rest of the document.
This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.