The reduction of 6‐methoxy‐9‐methyl‐11‐oxoechiboline using lithium aluminium hydride

Reduction of 6‐methoxy‐9‐methyl‐11‐oxoechiboline 1a using lithium aluminium hydride in boiling tetrahydrofuran under reflux affords 6‐methoxy‐9‐methylechiboline. However, attempts to effect a similar reduction of a suspension of compound 1a in boiling diethyl ether under reflux, in which it is only very slightly soluble, were unsuccessful and when, under these conditions, a Soxhlet apparatus was employed to effect dissolution, an unexpected reductive ring scission occurred along with reduction of the carbonyl group to afford 4a‐(2‐aminoethyl)‐6‐methoxy‐9‐methyl‐1,2,3,4,4a,9a‐hexahydrocarbazole 3 .