Erowid References Database
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Nichols DE, Barfknecht CF, Rusterholz DB, Benington F, Morin RD.
“Asymmetric synthesis of psychotomimetic phenylisopropylamines”.
J Med Chem. 1973 May;16(5):480-3.
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Abstract
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 analy- sis of enantiomeric purity was accomplished using a-methoxy-a-trifluoromethylphenylacetamides. Glc analysis of the N-trifluoroacetyl-S-prolylamides was used to confirm R-(-) and S-(+) absolute configurations of all compounds. (+)- or (-)-2,5dimethoxyamphetamine was brominated to give the (+)- or (-)-4-bromo compound. The enantiomers of 1,2,3,4-tetrahydro-2-naphthylamine could not be prepared by this method.
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