Synthesis of a deuterium‐labelled standard of bufotenine (5‐HO‐DMT) | Zendy

Wang YuYun | Zendy; Chen Chinpiao | Zendy

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Synthesis of a deuterium‐labelled standard of bufotenine (5‐HO‐DMT)

Author(s) -

Wang YuYun,

Chen Chinpiao

Publication year - 2007

Publication title -

journal of labelled compounds and radiopharmaceuticals

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.432

H-Index - 47

eISSN - 1099-1344

pISSN - 0362-4803

DOI - 10.1002/jlcr.1459

Subject(s) - chemistry , deuterium , stereochemistry , radiochemistry , nuclear physics , physics

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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