82301-19-7

Upstream product

• 3693-69-4 2-carbethoxy-2-azabicyclo<2.2.2>oct-5-ene 
• 5707-04-0 Phenylselenyl chloride 
• 3693-69-4 2-(Ethoxycarbonyl)-2-azabicyclo<2.2.2>oct-5-en 
• 113777-75-6 (1S,4S)-5-Chloro-6-phenylselanyl-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid ethyl ester 
• 113777-75-6 N-(ethoxycarbonyl)-5-chloro-6-(phenylselenenyl)-2-azabicyclo<2.2.2>octane 

Downstream Products

• 3885-76-5 N-carbethoxy-isoquinuclidin-6-one 
• 3885-76-5 2-Carboethoxy-(1S,4R)-2-azabicyclo[2.2.2]octan-6-one 

Relevant academic research and scientific papers

Synthesis and pharmacology of isoquinuclidine derivatives as 5-HT3 ligands

A series of 4-amino-5-chloro-2-methoxybenzoates and benzamides containing the 5- and 6-isoquinuclidinyl system was synthesised and evaluated for binding to 5-HT3, 5-HT4 and D2 receptors. In general, the isoquinuclidine derivatives at the 5-position have shown to be more potent as 5-HT3 ligands but they also possess 5-HT4 and D2 properties. However, the results show that the derivatives at the 6-position afforded the most promising compounds in terms of both receptor affinity and selectivity.

Regioselective Synthesis of Isoquinuclidin-6-ones. Synthesis of an Ibogamine Intermediate

Addition of benzeneselenenyl chloride to 5,6-dehydroisoquinuclidines 8 followed by dehydrohalogenation and hydrolysis of the derived vinyl selenides 11 affords isoquinuclidin-6-ones 7 regioselectively.The method has been applied to the synthesis of 7-syn-ethylisoquinuclidin-6-one 16, an intermediate in the synthesis of ibogamine 2a.