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Barfknecht, et al.
Journal of Medicinal Chemistry, 1973, Vol. 16, No. 5
Asymmetric Synthesis of Psycho tomimetic Phenylisopropylamines' David E. Nichols, Charles F. Barfknecht," David B. Rusterholz, Division ofMedicinal Chemistry, College of Pharmacy, The University of Iowa, Iowa city, Iowa 52242
Frederick Benington, and Richard D. Morin Neurosciences Research Program, The University of Alabama, Birmingham, Alabama 35294. Received October 24, 19 72
The enantiomers of a series of methoxy- and alkyl-substituted phenylisopropylamines were prepared by low-pressure reduction of imines formed by reaction of the appropriate phenylacetones with either (+)- or (-)-a-methylbenzylamine, followed by hydrogenolysis of the hydrochlorides of the resulting N-(a-phenethy1)phenylisopropylamines. Values of [ a]D are reported and enantiomeric purities were-in the range 96-99%. Overall yields ranged from 30 to 60%. Glc or fluorine nmr analysis of enantiomeric purity was accomplished using a-methoxyir-trifluoromethylphenylacetamides. Glc analysis of the N-trifluoroacetyl-Si-prolylamides was used to confirm R-( -) and S
