70243-51-5

Basic information

• Product Name: 9-Azabicyclo[3.3.1]nonan-3-ol, 9-(phenylmethyl)-, endo-
• CAS NO: 70243-51-5
• Molecular Formula: C15H21NO
• Molecular Weight: 231.338
• Mol File: 70243-51-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 9-Azabicyclo[3.3.1]nonan-3-ol, 9-(phenylmethyl)-, endo-(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Azabicyclo[3.3.1]nonan-3-ol, 9-(phenylmethyl)-, endo-(70243-51-5)
• EPA Substance Registry System: 9-Azabicyclo[3.3.1]nonan-3-ol, 9-(phenylmethyl)-, endo-(70243-51-5)

Safety Data

• Hazardous Substances Data: 70243-51-5(Hazardous Substances Data)

Upstream product

• 2291-58-9 9-benzyl-9-azabicyclo[3.3.1]nonan-3-one 

Downstream Products

• 363140-31-2 N-(9-benzyl-9-azabicyclo[3.3.1]nonan-3α-yl)-N'-(2-methoxy-5-methylphenyl)carbamate 
• 913815-84-6 N-(9-(6-aminodecyl)-9-azabicyclo[3.3.1]nonan-3α-yl)-N'-(2-methoxy-5-methylphenyl)carbamate 
• 1036759-20-2 (2-Methoxy-5-methyl-phenyl)-carbamic acid (1R,3R,5S)-9-[10-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-decyl]-9-aza-bicyclo[3.3.1]non-3-yl ester 
• 1036759-16-6 (2-Methoxy-5-methyl-phenyl)-carbamic acid (1R,3R,5S)-9-[6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-hexyl]-9-aza-bicyclo[3.3.1]non-3-yl ester 
• 913815-82-4 N-(9-(6-aminohexyl)-9-azabicyclo[3.3.1]nonan-3α-yl)-N'-(2-methoxy-5-methylphenyl)carbamate 
• 371226-28-7 O-(9-azabicyclo[3.3.1]nonan-3α-yl)-N-(2-methoxy-5-methylphenyl)carbamate 
• 504-12-1 exo-9-azabicyclo[3.3.1]nonan-3-ol 

Relevant articles and documents

Method for producing endo-9-azabicyclo[3.3.1]nonane-3-ol derivative

Provided is a method that makes it possible to obtain an endo-9-azabicyclo[3.3.1]nonane-3-ol derivative that is useful as an intermediate of agricultural and horticultural chemicals or pharmaceuticals at a low cost by reacting a 9-azabicyclo[3.3.1]nonane-3-on derivative with hydrogen under the presence of a catalyst comprising a ruthenium complex.

9-AZABICYCLO [3 . 3 . 1] NONANE DERIVATIVES AS MONOAMINE REUPTAKE INHIBITORS

The present invention relates to a 9-azabicyclo[3.3.1]nonane derivative of formula (I), wherein R1 is H or C1-5alkyl; X is O or NR2, wherein R2 is H, C1-5alkyl or C2-5acyl and Ar is C6-10aryl or a 5-10 membered heteroaryl ring system, both being optionally substituted with one to three of R3-R5 independently selected from halogen, C1-5alkyl, C1-5alkoxy, C3-6cycloalkyl, C2-5alkenyl, C2-5alkynyl, CN, NO2, hydroxy, phenyl, phenoxy and phenylC1-2alkoxy, wherein said C1-5alkyl and C1-5alkoxy are optionally substituted with one to three halogens and wherein said phenyl, phenoxy and phenylC1-2alkoxy are optionally substituted with one to three substituents independently selected from halogen and methyl or two of R3-R5 at adjacent positions together form a methylenedioxy or propylene unit, with the proviso that the compounds exo-9-methyl-3-phenoxy-9-azabicyclo[3.3.1]nonane and N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-1H indazole-5-amine are excluded, or a pharmaceutically acceptable salt or solvate thereof. The invention also relates to pharmaceutical compositions comprising said 9-azabicyclo[3.3.1]nonane derivatives and to their use in therapy.

Synthesis and sigma receptor binding affinities of 8-azabicyclo[3.2.1]octan-3α-yl and 9-azabicyclo[3.3.1]nonan-3α-yl phenylcarbamates

A series of N-(8-benzyl-8-azabicyclo[3.2.1]octan-3α-yl)carbamates and N-(9-benzyl-9-azabicyclo[3.3.1]nonan-3α-yl)carbamates was prepared and their affinities for sigma (σ1 and σ2) and serotonin 5-HT3 and 5-HT4 receptors was measured in vitro. The results of this structure-activity relationship study identified a novel compound, N-(9-benzyl-9-aza-bicyclo[3.3.1]nonan-3α-yl)N′- (2-methoxy-5-methylphenyl)carbamate (4i), having a high affinity and moderate selectivity for σ2 versus σ1 receptors and a low affinity for 5-HT3 and 5-HT4 receptors. The results of this structure-activity relationship study should provide valuable information for the preparation of σ2-selective ligands that can be used to further characterize the functional role of this receptor in vivo.