Acetylamino- 1-methoxytryptamines

A/b-Acetyl-5-acetylamino-l-methoxytryptamine (13) is prepared with an overall yield of 32% in eight steps from tryptamine (14, Scheme 3) [15]. M),l-Diacetyl-2,3-dihydrotryptamine (15) is obtained from 14 through Nb-acetylation (97%), reduction with Et3SiH/CF3COOH (98%) [16], and subsequent acetylation of N(l)-H (78%). 5-Nitro compound (16, 81%), ob-... 

Schemes Synthesis ofNb-acetyl-5-acetylamino-l-methoxytryptamine...

For the preparation of Nb-acetyl-6-acetylamino-l-methoxytryptamine (21) two routes have been developed (15). The first is seven steps from in-doUne (5) with an overall yield of 38%. The second is eight steps with a 34% overall yield starting from tryptamine (14). 

Scheme 4 Synthesis ofNb-acetyl-6-acetylamino-l-methoxytryptamine from indoline...

M)-Acetyl-5-acetylamino-l-methoxytryptamine (13) is of special interest because of its nature to change the reaction site depending on the nucleophile [33]. When 13 reacts with 2-naphthol in 85% HCOOH, Nb-acetyl-5-acetylamino-l-(2-hydroxynapht-l-yl)- (150,19%), Nb-acetyl-5-acetylamino-... 

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