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AI-extracted from the abstract
Characteristics
Synthetic chemistry paper
Peer reviewed
Topics
DMT
Keywords
Deuterium
Stereochemistry
Radiochemistry
Nuclear physics
Citations
6
Key points
Deuterium-labeled bufotenine was synthesized via the Batcho–Leimgruber strategy using lithium aluminum [2H4]-hydride to introduce four deuterium atoms.
Abstract
Abstract The Batcho–Leimgruber strategy was employed to synthesize 3‐(2‐dimethylamino‐[ 2 H 4 ]‐ethyl)‐1 H ‐indol‐5‐ol (bufotenine, 5‐HO‐DMT) ( 8 ) from commercial 3‐methyl‐4‐nitro‐phenol ( 1 ), benzyl bromide and N,N –dimethylformamide–dimethylacetal. Compound 4 was synthesized from compound 3 using the Batcho–Leimgruber strategy in the presence of Raney nickel and hydrazine hydrate. Compound 4 was treated with oxalyl chloride, dimethylamine and lithium aluminum [ 2 H 4 ]‐hydride to yield [2‐(5‐benzyloxy‐1 H ‐indol‐3‐yl)‐[ 2 H 4 ]‐ethyl]‐dimethyl‐amine ( 7 ). The benzyl ether in compound 7 was cleaved by hydrogenolysis to give bufotenine 8 . Copyright © 2007 John Wiley & Sons, Ltd.
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