Synthesis of S(+) and R(‐)‐3‐(2‐aminopropyl)indole from ethyl‐D‐ and L‐tryptophanate

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Abstract
A stereospecific requirement for hallucinogenesis applies to certain molecules containing an asymmetric center. Thus, only the R‐isomers of substituted phenylisopropylamines and lysergic acid diethylamide are psychotomimetic. The enantiomers of a minor hallucinogen, S(+)‐ and R(‐)‐3‐(2‐aminopropyl)indole (α‐methyltryptamine) (6a and 6b) were synthesized via a 5‐step manipulation from D‐ and L‐tryptophan ethyl ester hydrochloride, respectively. Optical purity of these two isomers was determined by pmr spectroscopy of their complexes with a europium chiral shift reagent using the indole C2 H signal.