Abstract
Reduction of the title compound (2) with diborane furnishes 1-trifluoroethyl-3-(2′-(trifluoroethylamino)ethyl)-3-vinylindoline (4), 1-hydroxy-trifluoroethyl-3-(2′-(trifluoroethylamino)ethyl)indole (5), and 1-methyl-2-trifluoroethyl-1,2,3,4-tetrahydro-β-carboline (6). However, treatment of2 with lithium aluminum hydride, H2/Pd on charcoal, and sodium borohydride affords hydroxyspiroindolenine8, hydroxy-bis(trifluoroacetyl)enaminospiroindoline9, andN-ethyltryptamine7, respectively. The results are discussed and the mechanisms of the reactions leading to4–8 are presented.
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