85506-18-9

Basic information

• Product Name: 8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 8-methyl-3-oxo-, methyl ester, (1R,2R,5S)-
• CAS NO: 85506-18-9
• Molecular Formula: C10H15NO3
• Molecular Weight: 197.234
• Mol File: 85506-18-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 8-methyl-3-oxo-, methyl ester, (1R,2R,5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 8-methyl-3-oxo-, methyl ester, (1R,2R,5S)-(85506-18-9)
• EPA Substance Registry System: 8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 8-methyl-3-oxo-, methyl ester, (1R,2R,5S)-(85506-18-9)

Safety Data

• Hazardous Substances Data: 85506-18-9(Hazardous Substances Data)

Upstream product

• 638-37-9 butanedial 
• 78315-99-8 acetone-1,3-dicarboxylic acid mono-methyl ester 
• 593-51-1 methylamine hydrochloride 
• 532-24-1 tropinone 
• 616-38-6 carbonic acid dimethyl ester 
• 77-92-9 citric acid 
• 17640-15-2 methyl cyanoformate 
• 100371-46-8 3-oxo-tropane-2,4-dicarboxylic acid dimethyl ester 
• 532-24-1 tropinone 
• 1830-54-2 3-oxopentanedioic acid dimethyl ester 
• 10521-08-1 pyran-2,4,6-trione 

Downstream Products

• 43021-26-7 methyl 8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate 
• 146725-34-0 O-456 
• 56620-28-1 (5S)-8-methyl-8-azabicyclo[3.2.1]octan-2-one 
• 484-93-5 ecgonidine 
• 180853-41-2 (1R,2R,3R,5S)-3-Benzoylamino-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester 

Relevant articles and documents

METHOD FOR THE PREPARATION OF N-MONOFLUOROALKYL TROPANES AND THEIR USE

The present invention relates to a method for the preparation of an N-monofluoroalkyl tropane, a method for the preparation of a trialkyltin tropane, a method for the preparation of an iodinated and/or radioiodinated tropane and the use of the N-monofluoroalkyl tropane as a precursor in the method for the preparation of the trialkyltin tropane and/or the iodinated and/or radioiodinated tropane.

Stereoselective deprotonation of tropinone and reactions of tropinone lithium enolate

Tropinone (6) was deprotonated with lithium diisopropylamide and with chiral lithium amides (18-24) and the resulting enolates (two enantiomers) were treated with electrophiles.The aldol reaction with benzaldehyde and deuteration were both diastereoselective.The former yielded only one isomer (exo, anti) of the aldol 8a; the latter proceeded from the exo face.This selectivity permitted us to probe the deprotonation of tropinone with lithium amides; it was concluded that the reaction involves predominantly the exo axial protons.The reaction of tropinone enolate with ethyl chloroformate led, via a ring opening, to the cycloheptenone derivative 9.The reaction with methyl cyanoformate yielded, in the presence of silver acetate and acetic acid, the β-ketoester 8b; however, in the absence of these additives, and especially when 12-crown-4 was added to the enolate, a ring opening leading to the pyrrolidine derivative 10 occured instead.Deprotonation of tropinone with chiral amides proceeded with modest enantioselectivity.A synthesis of non-racemic anhydroecgonine via this strategy allowed establishing the absolute stereochemistry of deprotonation.