112574-77-3

Basic information

• Product Name: Methyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate
• Synonyms: Methyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate;methyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate hydrochloride
• CAS NO: 112574-77-3
• Molecular Formula: C₁₀H₁₅NO₃
• Molecular Weight: 197.23
• Mol File: 112574-77-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 294.1±35.0 °C(Predicted)
• Appearance: /
• Density: 1.173±0.06 g/cm3(Predicted)
• PKA: 10.89±0.20(Predicted)
• CAS DataBase Reference: Methyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate(112574-77-3)
• EPA Substance Registry System: Methyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate(112574-77-3)

Safety Data

• Hazardous Substances Data: 112574-77-3(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 43021-26-7 methyl 8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate 
• 46255-79-2 methyl (endo, endo)-3-hydroxy-8-methyl-8-azabicyclo<3.2.1>octan-2-carboxylate 
• 7143-09-1 methyl (2-endo, 3-exo)-3-hydroxy-8-methyl-8-azabicyclo<3.2.1>octan-2-carboxylate 

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.