913255-92-2

Basic information

• Product Name: (-)-(1R)-8-phenylisoneomenthyl (1R,3-exo)-2-benzyl-2-azabicyclo[2.2.1]heptane-3-carboxylate
• CAS NO: 913255-92-2
• Molecular Weight: 445.645
• Mol File: 913255-92-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (-)-(1R)-8-phenylisoneomenthyl (1R,3-exo)-2-benzyl-2-azabicyclo[2.2.1]heptane-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(1R)-8-phenylisoneomenthyl (1R,3-exo)-2-benzyl-2-azabicyclo[2.2.1]heptane-3-carboxylate(913255-92-2)
• EPA Substance Registry System: (-)-(1R)-8-phenylisoneomenthyl (1R,3-exo)-2-benzyl-2-azabicyclo[2.2.1]heptane-3-carboxylate(913255-92-2)

Safety Data

• Hazardous Substances Data: 913255-92-2(Hazardous Substances Data)

Upstream product

• 104870-80-6 (1R,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol 
• 129214-96-6 (-)-8-phenylneoisomenthyl glyoxylate 
• 215321-42-9 Chloro-oxo-acetic acid (1R,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Downstream Products

• 212073-04-6 (+)-(1R)-2-benzyl-3-(diphenylmethylidene)-2-azabicyclo[2.2.1]heptane 
• 212073-06-8 (+)-(1R)-2-benzyl-2-azabicyclo[2.2.1]heptan-3-one 
• 192461-74-8 (+)-(1R,3-exo)-2-benzyl-3-[(hydroxy)diphenylmethyl]-2-azabicyclo[2.2.1]heptane 

Relevant articles and documents

The use of (-)-8-phenylisoneomenthol and (-)-8-phenylmenthol in the enantioselective synthesis of 3-functionalized 2-azabicyclo[2.2.1]heptane derivatives via aza-Diels-Alder reaction

The asymmetric aza-Diels-Alder reaction of the (1R)-8-phenylmenthyl or (1R)-8-phenylisoneomenthyl glyoxylate-derived N-benzylimine with cyclopentadiene resulted in the enantioselective synthesis of the corresponding pure [(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylates (80 or 69% yield, respectively). Reduction of these cycloadducts with LiAlH4 afforded pure (-)-[(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-yl]methanol. Furthermore, a reaction sequence based on Barbier-Wieland degradation of both (1S,3-exo)-adducts afforded pure (+)-(1R)-2-benzoyl-2-azabicyclo[2.2.1]heptan-3-one. In the course of the two transformation sequences referred, the chiral auxiliaries were recovered in a virtually quantitative way.