The innovation engine for new materials

Miranda Sroda

Miranda Sroda




University of California San Diego


David Fisher

Faculty Sponsor(s): 

Javier Read de Alaniz

Faculty Sponsor's Department(s): 

Chemistry and Biochemistry

Project Title: 

The Synthesis of Sterically Hindered Amines For the Creation of Pharmaceutical Drugs

Project Description: 

Sterically hindered anilines are important to medicinal chemists due to their ability to increase the lipophilicity and

metabolic stability of drug molecules. Current methodologies for the synthesis of hindered anilines often require

harsh basic and acidic conditions and can be limited by over alkylation. We utilize a new methodology that

overcomes these drawbacks and uses readily available starting material and abundant copper salt catalysts in a

radical coupling reaction. We synthesize sterically hindered anilines through a radical mediated coupling process

using alkyl halides and nitrosoarenes. This reaction occurs under mild reaction conditions with high functional

group tolerance. We are currently developing an intramolecular process to access amino alcohols of various

substituents. Currently we have synthesized amino alcohols utilizing the following nitroso compounds: 1-methoxy-

4-nitrosobenzene, methyl 4-nitrosobenzoate, 1,3-dimethyl-5-nitrosobenzene, 1-iodo-2-nitrosobenzene, 1-chloro-3-

nitrosobenzene, and 1-bromo-4-nitrosobenzene. The compounds are purified using column chromatography and

characterized using NMR, Mass Spectroscopy and IR. We anticipate constructing a library of small molecules with

a variety of functional groups using this process. This work will be applied in synthesizing new pharmaceutical