1613740-59-2

Upstream product

• 1006-94-6 5-methoxylindole 
• 452096-18-3 [((1S,2R)-2-Chloro-1-methyl-2-phenyl-ethyl)-methyl-amino]-acetonitrile 
• 452096-19-4 pseudoephedrine-derived chloride 

Downstream Products

• 1613740-73-0 (3S,4R)-6-Methoxy-2,3-methyl-4-phenyl-1,2,3,4-tetrahydro-β-carboline 

Relevant academic research and scientific papers

Alkylation of indoles by aziridinium ions: New rapid access to tetrahydro-β-carbolines (THBCs)

The alkylation of indoles by aziridinium ions generated in situ from β-amino chlorides was explored. The outcome of this reaction strongly relied on the substitution pattern of the starting β-amino chloride and requires silver tetrafluoroborate activation to proceed in reasonable yield. Ephedrine- and pseudoephedrine-derived N-cyanomethyl-β-amino chlorides afforded the corresponding tryptamines in a regio- and stereoselective manner and subsequent silver(I)-promoted Pictet-Spengler reactions produced 4-phenyl substituted THBCs in good yields. Unexpected epimerization at C-3 was found in these reactions, producing trans-3,4-disubstituted THBCs stereoselectively.