36127-54-5

Usage

Uses

Used in Organic Synthesis:
8-methyl-8-azabicyclo[3.2.1]octan-2-ol is used as a building block for the synthesis of more complex organic molecules due to its unique structure and properties.
Used in Medicinal Chemistry:
8-methyl-8-azabicyclo[3.2.1]octan-2-ol is used as a potential candidate for drug development due to its pharmacological activities and structural features that make it a valuable compound for research and development purposes.

Upstream product

• 5964-12-5 (+/-)-2exo,3exo-epoxy-tropane 
• 60-29-7 diethyl ether 
• 125217-79-0 N-methyl-6β-(phenylsulphonyl)-8-azabicyclo<3.2.1>oct-3-en-2-one 
• 123686-89-5 (1RS)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carbonitrile 
• 99020-85-6 (+/-)-Anhydroecgonine amide 
• 13612-59-4 cyclohepta-2,4,6-triene-1-carbonitrile 
• 25065-00-3 1-methyl-pyridinium-3-olate 
• 125217-81-4 (1S,2S,5S,6R)-6-Benzenesulfonyl-8-methyl-8-aza-bicyclo[3.2.1]octan-2-ol 
• 825-26-3 2α-hydroxytropan-3-one 
• 78477-91-5 8-methyl-8-azabicyclo[3.2.1]octan-2-one 
• 78386-53-5 phenyl 8-azabicycl<3.2.1>oct-2-ene-8-carboxylate 
• 529-18-0 tropidine 
• 125217-81-4 (1S,2R,5S,6R)-6-Benzenesulfonyl-8-methyl-8-aza-bicyclo[3.2.1]octan-2-ol 
• 78386-54-6 phenyl 2β,3β-epoxy-8-azabicycl<3.2.1>octane-8-carboxylate 

Downstream Products

• 95534-02-4 (1R,2R,5S)-2-Acetoxy-8,8-dimethyl-8-azonia-bicyclo[3.2.1]octane; iodide 
• 64530-37-6 Acetic acid (1R,2R,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-yl ester 
• 78386-52-4 3-acetonyl-2-methyl-2-azabicyclo<2.2.2>octane 
• 78386-47-7 tropan-2β-yl toluene-p-sulphonate 
• 64530-37-6 Acetic acid (1R,2S,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-yl ester 
• 87395-57-1 (+)-2α-tropanyl chlorodiphenylacetate 
• 87395-55-9 (+)-2α-tropanyl 1-azaphenothiazine-10-carboxylate 

Relevant academic research and scientific papers

1,3-Dipolar Cycloaddition of 1-Methyl-3-oxidopyridinium and Sulfonylethenes. A Synthesis of 2-Tropanols and Monofluorinated 2-Tropanol

2α- and 2β-Tropanols were synthesized by 1,3-dipolar cycloaddition of phenyl vinyl sulfone and 1-methyl-3-oxidopyridinium regio- and stereoselectively.The method was extended to a preparation of 6α-fluoro-2β-tropanol from 1-(benzenesulfonyl)-1-fluoroethene.

REDUCTIVE TRANSFORMATION OF A HYDROXYIODOKETONE OF 8-AZABICYCLOOCTANE INTO 7-AZABICYCLOHEPTANE WITH LITHIUM ALUMINIUM HYDRIDE

1α,4β-Diodo-2α-acetoxytropan-3-one (2) and 1α-iodo-2α-acetoxytropan-3-one (3), which comprise 64percent of products emerging from the lead tetraacetate oxidation of tropan-3α-ol in presence of iodine, were subjected to lithium aluminium hydride reduction.The expected 2.3-dihydroxytropane was not obtained.Instead, a diol which was not prone to periodate oxidation, containing one primary and one secondary alkoholic groups was obtained.It was assigned the 1-hydroxymethyl-2α-hydroxy-7-methyl-7-azabicycloheptane structure (8), on the basis of spectroscopic evidences (ir, nmr and mass spectrometry) and some chemical transformations heptane (12)>.The reaction is understood as an initial β-elimination process, triggered by the delivery of hydride ion to the carbonyl function in the sequence 3 21 22, yielding a highly reactive enolate aldehyde (22) which is prone to an immediate internal aldol condensation (22) (23) (24), affording the observed diol (8) on further reduction of the a aldehydic group by LiALH4.The reductive deiodination of (3) into 2α-acetoxytropine (2b) or into 2α-hydroxytropan-3-one (25) was smoothly achieved by means of hydrogenation over Raney Nickel on mild basic conditions.

Solvolytic Rearrangements of Azabicyclic Compounds. Part 2. Kinetics

Rates of solvolysis in aqueous ethanol and aqueous dioxan of three 2-exo-chloroazabicycloalkanes have been studied and first-order rare constants are derived and compared with published values for analogous compounds.Anchimeric assistance by the bridge N-atom is evidently not important in the rate-controlling step in these rearrangements, though it may occur to a minor extent in the case of 2-exo-chloro-7-methyl-7-azanorbornane.Solvolytic results for tropan-2β-yl toluene-p-sulphonate in aqueous ethanol and aqueous acetone mixtures are also reported and compared with literature data for the carbobicyclic and oxabicyclic analogues.