Premium
The reduction of 6‐methoxy‐9‐methyl‐11‐oxoechiboline using lithium aluminium hydride
Author(s) -
Cox Brian,
Robinson Brian
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250144
Subject(s) - chemistry , tetrahydrofuran , aluminum hydride , lithium (medication) , lithium aluminium hydride , boiling , diethyl ether , aluminium , medicinal chemistry , ether , hydride , dissolution , alcohol , ring (chemistry) , organic chemistry , methanol , solvent , metal , medicine , endocrinology , methoxide
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 .