36127-54-5

Basic information

• Product Name: 8-methyl-8-azabicyclo[3.2.1]octan-2-ol
• CAS NO: 36127-54-5
• Molecular Formula: C₈H₁₅NO
• Molecular Weight: 141.2108
• Mol File: 36127-54-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 213.8°C at 760 mmHg
• Flash Point: 80.4°C
• Density: 1.078g/cm³
• Vapor Pressure: 0.0355mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: 8-methyl-8-azabicyclo[3.2.1]octan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 8-methyl-8-azabicyclo[3.2.1]octan-2-ol(36127-54-5)
• EPA Substance Registry System: 8-methyl-8-azabicyclo[3.2.1]octan-2-ol(36127-54-5)

Safety Data

• Hazardous Substances Data: 36127-54-5(Hazardous Substances Data)

Usage

Description

8-methyl-8-azabicyclo[3.2.1]octan-2-ol is a bicyclic azabicyclo compound with a nitrogen atom in the ring and a hydroxyl group attached to the second carbon of the bicyclic structure. It belongs to the family of azabicyclo compounds and has unique structural and chemical properties that make it a versatile intermediate in organic synthesis and a potential candidate for drug development.

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

• 56620-28-1 (5S)-8-methyl-8-azabicyclo[3.2.1]octan-2-one 
• 78477-91-5 8-methyl-8-azabicyclo[3.2.1]octan-2-one 
• 78386-54-6 phenyl 2β,3β-epoxy-8-azabicycl<3.2.1>octane-8-carboxylate 
• 125217-81-4 (1S,2R,5S,6R)-6-Benzenesulfonyl-8-methyl-8-aza-bicyclo[3.2.1]octan-2-ol 
• 5964-12-5 (+/-)-2exo,3exo-epoxy-tropane 
• 60-29-7 diethyl ether 
• 25065-00-3 1-methyl-pyridinium-3-olate 
• 125217-79-0 N-methyl-6β-(phenylsulphonyl)-8-azabicyclo<3.2.1>oct-3-en-2-one 
• 13612-59-4 cyclohepta-2,4,6-triene-1-carbonitrile 
• 529-18-0 tropidine 
• 99020-85-6 (+/-)-Anhydroecgonine amide 
• 78386-53-5 phenyl 8-azabicycl<3.2.1>oct-2-ene-8-carboxylate 
• 123686-89-5 (1RS)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carbonitrile 
• 825-26-3 2α-hydroxytropan-3-one 

Downstream Products

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

Relevant articles and documents

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.