173425-93-9

Upstream product

• 20513-09-1 (1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 51-34-3 scopolamine 

Downstream Products

• 946434-23-7 C₂₂H₃₅NOSi 
• 946434-24-8 C₃₆H₆₂N₂O₂Si₂ 
• 946434-25-9 C₂₃H₃₇NO₂Si 
• 946434-42-0 C₁₆H₃₁NOSi 
• 946434-41-9 C₂₂H₄₁NOSi 
• 946434-43-1 C₂₈H₅₁NOSi 
• 946434-26-0 C₂₃H₃₄F₃NOSi 
• 946434-28-2 C₂₃H₃₇NOSi 
• 946434-27-1 C₂₂H₃₄BrNOSi 
• 1357384-46-3 (2S,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-2-((Z)-2-(4-methoxyphenoxy)vinyl)-1-methyl-6-vinylpiperidine 
• 343317-08-8 (1S,3R,5S)-8-Methyl-8-aza-bicyclo[3.2.1]octane-1,3-diol 

Relevant academic research and scientific papers

Synthesis and nicotinic receptor activity of a hydroxylated tropane

(±)-3α-Hydroxy homoepibatidine 4 has been synthesized from the alkaloid scopolamine 5 and its properties as a nicotinic agonist assessed. While still binding strongly, the compound showed reduced agonist potency for the α4β2 nAChR compared with the parent compound epibatidine 1. Compound 4 also displayed generally similar binding and selectivity profiles at α4β2, α 2β4, α3β4, and α4β4 nAChR subtypes to those for nicotine.

A Meisenheimer rearrangement approach to bridgehead hydroxylated tropane alkaloid derivatives

Thermolysis of 3-t-butyldimethylsiloxy-8-methyl-8-azabicyclo[3.2.1]oct-6-ene N-oxide (11) and (12) in butyronitrile gave 3-t-butyldimethylsiloxy-9-methyl-8-oxa-9-azabicyclo[3.2.2]non-6-ene (13) which upon reductive N-O ring cleavage, hydrogenation, oxidation and deprotection yielded the 3-hydroxy analogue 8-methyl-8-azabicyclo[3.2.1]octane-1,3-diol (6a ? 6b) of the tropane alkaloid physoperuvine.