1314098-76-4

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 98062-25-0 tert-butyl N-[2-(3,4-dimethoxyphenyl)ethyl]carbamate 
• 66384-48-3 2-(2-iodo-4,5-dimethoxyphenyl)ethan-1-amine 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 66384-45-0 N-acetyl-2-iodo-4,5-dimethoxy-β-phenethylamine 
• 6275-29-2 N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide 
• 1384186-28-0 N-2-(2-iodo-4,5-dimethoxyphenyl)ethyl-tert-butoxycarbonylacetamide 

Downstream Products

• 1026016-83-0 ((3R,11bR)-3-isobutyl-9.10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one) 
• 1228458-05-6 (5S,6R,E)-6-(tert-butyldimethylsilyloxy)-5-isobutyl-10,11-dimethoxy-2,3,5,6-tetrahydrobenzo[d]azecin-4(1H)-one 
• 1384186-23-5 C₅₂H₈₆N₂O₈Si₂ 
• 1228458-10-3 (2R,3S,11bR)-2-hydroxy-3-isobutyl-9,10-dimethoxy-2,3,6,7-tetrahydro-1H-pyrido[2,1-α]isoquinolin-4(11bH)-one 
• 1384186-29-1 C₄₀H₅₈N₂O₈ 
• 1384186-18-8 2-(4,5-dimethoxy-2-vinylphenyl)ethanamine 
• 1384186-21-3 (2S,3R)-3-((tert-butyldimethylsilyl)oxy)-N-(4,5-dimethoxy-2-vinylphenethyl)-2-isobutylpent-4-enamide 
• 203806-39-7 N-(tert-butoxycarbonyl)-2-(4,5-dimethoxy-2-vinylphenyl)ethylamine 
• 66384-48-3 2-(2-iodo-4,5-dimethoxyphenyl)ethan-1-amine 

Relevant academic research and scientific papers

Synthesis of N-Boc-C1 vinyl tetrahydroisoquinoline via Zn-mediated intramolecular cyclization of N-Boc protected iodo acetonide

The Zn-mediated elimination of N-Boc protected iodo acetonide undergoes intramolecular cyclization to afford N-Boc-C1 vinyl tetrahydroisoquinoline in good yield.

Synthesis and Biological Evaluation of Endocannabinoid Uptake Inhibitors Derived from WOBE437

WOBE437 ((2E,4E)-N-(3,4-dimethoxyphenethyl)dodeca-2,4-dienamide, 1) is a natural product-derived, highly potent inhibitor of endocannabinoid reuptake. In this study, we synthesized almost 80 analogues of 1 with different types of modifications in the dodecadienoyl domain as well as the dimethoxyphenylethyl head group, and we investigated their effects on anandamide uptake into U937 cells. Intriguingly, none of these analogues was a more potent inhibitor of anandamide uptake than WOBE437 (1). At the same time, a number of WOBE437 variants exhibited potencies in the sub-100 nM range, with high selectivity over inhibition of the endocannabinoid-degrading enzyme fatty acid amide hydrolase; two compounds were virtually equipotent with 1. Interestingly, profound activity differences were observed between analogues in which either of the two methoxy substituents in the head group had been replaced by the same bulkier alkoxy group. Some of the compounds described here could be interesting departure points for the development of potent endocannabinoid uptake inhibitors with more drug-like properties.

PROCESSES AND REAGENTS FOR MAKING DIARYLIODONIUM SALTS

This disclosure relates to processes and reagents for making diaryliodonium salts, which are useful for the preparation of fluorinated, iodinated, astatinated and radiofluorinated aromatic compounds.

A ring-closing metathesis-based approach to the synthesis of (+)-tetrabenazine

A modular stereoselective synthesis of the vesicular monoamine transport inhibitors (+)-tetrabenazine ((+)-1) and (+)-α-dihydrotetrabenazine ((+)-2) has been developed. The approach is based on amine 4 and acid 5 as the key building blocks, which were elaborated into macrolactam 3 by amide coupling and a subsequent highly E-selective RCM reaction. Macrolactam 3 could be converted into tetrabenazine in three known steps.