Synthesis and Resolution of (-)-5-methoxy-N-propyl-1,2,3,4-tetrahydronapthalen-2-amine, a Key Intermediate for the Development of an Antiparkinsonian Drug
Murray, Michael R., 1990-
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Commercially available 1,6-dihydroxynapthalene was used as starting material to synthesize and resolve the (-)-5-methoxy-N-propyl-1,2,3,4-tetrahydronapthalen-2-amine, a key intermediate for development of antiparkinsonian drugs. The synthesis process was completed on a small scale to observe expected results before being repeated with a more substantial amount of reagents. The resolution of a racemic mixture of products using a (+)-chlocyphos enantiomer led to the desired stereoisomerism that has been found effective for targeting receptors in the brains of Parkinson patients. The synthesis was completed in a way that required careful step-wise mechanisms and extensive purification in order to obtain the desired final product, identified by 1H NMR analysis.