157008-48-5

Basic information

• Product Name: (1R)-N-methyl-2β-methoxycarbonyl-3α-(4-fluorophenyl)-8-azabicyclo[3.2.1]octane
• Synonyms: (1R)-N-methyl-2β-methoxycarbonyl-3α-(4-fluorophenyl)-8-azabicyclo[3.2.1]octane
• CAS NO: 157008-48-5
• Molecular Weight: 277.339
• Mol File: 157008-48-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (1R)-N-methyl-2β-methoxycarbonyl-3α-(4-fluorophenyl)-8-azabicyclo[3.2.1]octane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-N-methyl-2β-methoxycarbonyl-3α-(4-fluorophenyl)-8-azabicyclo[3.2.1]octane(157008-48-5)
• EPA Substance Registry System: (1R)-N-methyl-2β-methoxycarbonyl-3α-(4-fluorophenyl)-8-azabicyclo[3.2.1]octane(157008-48-5)

Safety Data

• Hazardous Substances Data: 157008-48-5(Hazardous Substances Data)

Upstream product

• 53-21-4 (-)-cocaine hydrochloride 
• 5796-31-6 ecgonine hydrochloride 
• 168143-65-5 methyl (1R,5S)-8-methyl-3-(((trifluoromethyl)sulfonyl)oxy)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate 
• 85506-18-9 (1R)-(-)-2-carbomethoxy-3-tropinone 
• 352-13-6 4-flourophenylmagnesium bromide 
• 50373-10-9 methyl ecgonidine 
• 67-56-1 methanol 
• 184376-51-0 (1R,2R,3R,5S)-3-(4-Fluoro-phenyl)-8-methyl-2-(3-methyl-[1,2,4]oxadiazol-5-yl)-8-aza-bicyclo[3.2.1]octane 
• 168254-92-0 (1R,2S,3R,5S)-(p-fluorophenyl)-2-(3'-methyl-1',2',4-oxadiazol-5'-yl)tropane 
• 168143-68-8 O-1104 

Downstream Products

• 306740-65-8 (1R)-2β-(1-propanoyl)-3α-(4-fluorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane 
• 306740-67-0 (1R)-2β-(1-propanoyl)-3α-(4-fluorophenyl)-8-azabicyclo[3.2.1]octane 
• 306740-69-2 N-[2-(3'-N'-propyl-(1''R)-3''α-(4-fluorophenyl)tropane-2''β-(1-propanoyl))((2-((triphenylmethyl)thio)ethyl)amino)acetyl]-S-(triphenyl)-2-aminoethanethiol 
• 201472-88-0 (1R,2S,3R,5S)-2-(Benzo[1,3]dioxol-5-yloxymethyl)-3-(4-fluoro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octane 
• 850888-35-6 (1R)-2β-[(3,4-methylenedioxy)phenoxy]methyl-3α-(4-fluorophenyl)-8-(4-methyl benzenesulfonyl)tropane 
• 850888-33-4 (1R)-2β-carbomethoxy-3α-(4-fluorophenyl)-8-(4-methyl benzenesulfonyl)tropane 
• 850888-34-5 (1R)-2β-hydroxymethyl-3α-(4-fluorophenyl)-8-(4-methyl benzenesulfonyl)tropane 
• 306740-94-3 (1R)-2β-methoxycarbonyl-3α-(4-fluorophenyl)-8-azabicyclo[3.2.1]-octane 
• 306740-63-6 (1R)-2β-carboxylic acid methoxymethylamide-3α-(4-fluorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane 
• 201472-82-4 [(1R,2S,3R,5S)-3-(4-Fluoro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-yl]-methanol 

Relevant articles and documents

Copper-mediated nucleophilic radiofluorination of [18F]β-CFT for positron emission tomography imaging of dopamine transporter

[18F]β-CFT is a positron emission tomography (PET) ligand for imaging of dopamine transporter. It was proved to be a sensitive PET marker to detect presynaptic dopaminergic hypofunction in Parkinson's disease. In recent years, copper-mediated 18F-fluorination of aryl boronic esters has been successful in some molecules containing aromatic groups. In this study, we describe the novel synthetic strategy of [18F]β-CFT by copper-mediated nucleophilic radiofluorination with pinacol-derived aryl boronic esters upon reaction with [18F]KF/K222 and Cu (OTf)2(py)4. The radiolabeling protocol was optimized with [18F]fluoride elution method and amount of copper catalyst used. [18F]β-CFT is obtained from boronic ester precursors in 2.2% to 10.6% non-isolated radiochemical yield (RCY). Purified [18F]β-CFT with >99% radiochemical purity (RCP) and high molar activity was obtained in validation runs. The radiolabeling procedure is straightforward and can easily be adapted for clinical use.

Intermediates for the synthesis of radiolabelled tropanes

The compounds of the present invention comprise a tropane compound or ligand that selectively binds to tropane recognition sites, e.g., neuron transporters such as that DAT. The tropane ligand is radiolabeled with a radioactive technetium or rhenium by a chelating ligand which is attached to the tropane ligand by a linker. Tropane compounds or ligands useful in the pratice of the present invention can generally be represented by formula II where R1 and R2 are defined as above and where R1 can also be substituted at the C4 position of the tropane ring: Any tropane compound of the general formula II is useful in the present invention so long as it binds to DAT. Useful tropane analogs have a 3α-group,i.e., are of the boat configuration. Intermediates for the synthesis of the radiolabeled tropanes are claimed.

Synthesis and ligand binding of tropane ring analogues of paroxetine

(3S,4R)-4-(4-Fluoropheny)-3-[[3,4- (methylenedioxy)phenoxy]methyl]piperidine [(3S,9R)-3, paroxetine] is a selective serotonin reuptake inhibitor (SSRI) used as an antidepressant in humans. In previous studies, we reported that certain (1R)-3β-(substituted