Synthesis of isotryptamines and tetrahydro-?-carbolines from 2-indolylacetic acid derivatives

The reaction of ethyl 2-indolylacetate with alkylamines gave the corresponding amides, which were reduced with sodium borohydride to isotryptamines. The latter were converted to 1,2,3,4-tetrahydro-γ-carboline derivatives by condensation with formaldehyde.