Synthesis of Selenopsilocine (3-Dimethylaminoethyl-4-hydroxybenzo[b]selenophene)

Starting from the known 6-methoxyanthranilic acid (51, we have synthesized in six steps the selenium analogue of psilocine (112).The key intermediate is the 4methoxyselenoindoxyl ( a ) , which is condensed with the d i m e t h y l a m i n o c a r b a m o y l m e t h y l e n e t r i p ~y l p h o s p h o r a n to give the aromatic amide (9a).Its reduction with lithium aluminium hydride leads to the methoxyamine (9b) which is finally demethylated by sodium ethanethiolate to lc.