32991-04-1

Upstream product

• 2581-34-2 3-methyl-4-nitrophenol 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 22424-58-4 5-benzyloxy-2-nitrotoluene 
• 100-39-0 benzyl bromide 

Downstream Products

• 250739-31-2 C₁₇H₁₉NO₅ 
• 250739-30-1 4-amino-3-(2,2-dimethoxy-ethyl)-phenol 
• 1215-59-4 5-benzyloxy-1H-indole 

Relevant academic research and scientific papers

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

The Batcho-Leimgruber strategy was employed to synthesize 3-(2-dimethylamino-[2H4]-ethyl)-1H-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 [2H4]-hydride to yield [2-(5-benzyloxy-1H-indol-3-yl)-[2H4]-ethyl] -dimethyl-amine (7). The benzyl ether in compound 7 was cleaved by hydrogenolysis to give bufotenine 8. Copyright

A novel safety-catch linker for the solid-phase synthesis of amides and esters

(matrix presented) A new safety-catch linker for solid-phase organic synthesis is described. Synthesis and attachment of the linker to the solid phase was achieved via a simple and high-yielding strategy. The linker was exemplified by acylation to form unactivated amides, activation of the linker, and cleavage to release acyl moieties. Acids, amides, or esters were released under mild conditions and with exceptionally high purity. The reactivities of unactivated and activated amides are compared.

Intermediates for indoles

Ortho-nitrotoluenes are condensed with formamide acetals to yield the corresponding otho-nitro-β-aminestyrenes which undergo cyclization upon reduction to yield indoles.