Office of Technology Transfer – University of Michigan

Preparation and Uses of 1-Aminonorbornanes

Technology #7527

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Researchers
Corey Stephenson
Managed By
Jeremy Nelson

The technology enclosed is a novel and efficient methodology to obtain (un)substituted 1-aminonorbornanes (bicyclo[2.2.1]heptanes), from aminocyclopropane starting materials, through photoredox catalysis. The technology can be employed with current light-mediated batch and continuous flow processing technologies, affording gram-scale quantities.

The products that can be obtained from this technology are expected to be valuable for drug development and discovery campaigns. The 1-aminonorbornane functional group is proposed to replace traditional aromatic motifs, which are thought to be responsible for high drug attrition rates. 1-aminonorbornanes can potentially provide improved pharmacokinetic (PK) and pharmacodynamics (PD) profiles as well as a more metabolically stable functional group.

The aniline moiety is an ideal example of an existing metabolically labile functional group that could be replaced by 1-aminonorbornanes. Analysis of drugs withdrawn for undesirable toxicities estimates that aniline functional groups are present in ~50% of these drugs. As a bioisostere offering similar shape and physicochemical properties to the aniline moiety, the implementation of 1-aminonorbornane functionalities into drugs or drug leads can provide a functionality that has improved properties.

Currently, many methods that yield 1-aminobornanes exist. However, most of the current methodologies are limited in scope, significantly restricting the versatility of substitution and the implementation of the 1-aminonorbornane functional group in drug discovery and development efforts. This technology is an improved route to obtain (un)substituted 1-aminonorbornanes.

A photoredox catalyzed method to obtain norbornanes with bridgehead amine substitutions using batch and continuous flow processing

The technology is a novel synthetic visible light-mediated route to obtain (un)substituted 1-aminonorbornanes using both batch and continuous flow processing. The technology employs a heteroleptic iridium (III) complex, simple Lewis acidic salt additives, and irradiation with visible light.

Applications

  • Starting material(s) for commercialization
  • Improve feasibility for large-scale syntheses of unsubstituted and substituted 1-aminonorbornanes

Advantages

  • Batch and continuous flow processing
  • Large reaction scope
  • Gram quantity scale
  • Mild reaction = conditions