139228-24-3

Basic information

• Product Name: (+/-)-2,5β-methano-1H-3aα,6aα-cyclopenta[c]pyrrol-4α-amine
• CAS NO: 139228-24-3
• Molecular Weight: 138.213
• Mol File: 139228-24-3.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-2,5β-methano-1H-3aα,6aα-cyclopenta[c]pyrrol-4α-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-2,5β-methano-1H-3aα,6aα-cyclopenta[c]pyrrol-4α-amine(139228-24-3)
• EPA Substance Registry System: (+/-)-2,5β-methano-1H-3aα,6aα-cyclopenta[c]pyrrol-4α-amine(139228-24-3)

Safety Data

• Hazardous Substances Data: 139228-24-3(Hazardous Substances Data)

Upstream product

• 139255-60-0 (3aS,4S,5S,6aR)-5-Hydroxymethyl-4-(toluene-4-sulfonylamino)-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester 
• 139255-60-0 (3aS,4S,5R,6aR)-5-Hydroxymethyl-4-(toluene-4-sulfonylamino)-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester 
• 139228-14-1 (3aS,4S,5S,6aR)-4-(Toluene-4-sulfonylamino)-5-(toluene-4-sulfonyloxymethyl)-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester 
• 139228-13-0 (3aS,4S,6aR)-5-Methylene-4-(toluene-4-sulfonylamino)-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester 
• 139228-12-9 tert-butyl (3aR,6aS)-5-methylene-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate 
• 139255-61-1 N-(3S,4R,5R,7R)-1-Aza-tricyclo[3.3.1.0^3,7]non-4-yl-4-methyl-benzenesulfonamide 

Relevant articles and documents

Enantioselective synthesis of dual 5-HT4/5-HT3 serotonergic azanoradamantane SC-52491

A racemic synthesis of azanoradamantane (±)-3 was accomplished via Yamamoto's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen's asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e.

USE OF ATOM-TRANSFER RADICAL CYCLIZATIONS AS AN EFFICIENT ENTRY INTO A NEW "SEROTONERGIC" AZANORADAMANTANE

A route to azanoradamantanes is described which makes use of an atom-transfer radical cyclization to afford 3-azabicycloocatanes 3A and 3B.Subsequent elaboration of exo-allylamine functionality, followed by cyclization of the endo-hydroxymethyl intermediate 9, affords the new azanoradamantanes 11 and 4.This new azatricyclic system is useful for producing serotonin 5-HT3 antagonists and 5-HT4 agonists. Key words: Azanoradamantane; 3-azabicyclooctane; serotonin