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Thursday, August 27 • 4:40pm - 5:20pm
[0093] Synthesis of a Heterocyclic Pharmaceutical Intermediate via an Intramolecular Asymmetric [3+2] Nitrone/Olefin Cycloaddition

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A scalable, asymmetric synthesis of (3aS,6aS)-6a-(5-bromo-2-fluorophenyl)-1-((R)-1-phenylpropyl)tetrahydro-1H,3H-furo[3,4-c]isoxazole (1), a key intermediate in the synthesis of LY2886721 is reported.  Highlights of the synthesis include: (1) The development of an asymmetric [3+2] intramolecular cycloaddition through a combined kinetic modeling and experimental approach; (2) The development of a new synthesis of (R)-N-(1-phenylpropyl)hydroxylamine tosylate (2) which proceeds through a p-anisaldehyde imine and avoids the formation of toxic hydrogen cyanide gas as a by-product.  Results of a synthesis executed on the multi-100 kg scale (which proceeded in 36% overall yield) will be discussed.

Invited Lecturers
avatar for Stan Kolis

Stan Kolis

Research Advisor, Small Molecule Design and Development, Eli Lilly and Company
Working in design and development of small molecule API Synthetic routes for transfer to commercial development. Led a group of chemists and engineers whose primary task was kinetic reaction modeling. Also have oversight for the Lilly Process Safety Lab.

Thursday August 27, 2015 4:40pm - 5:20pm
MCC Theater