Umpolung Flow Chemistry for the Synthesis of a 3-Oxo-3H-spiro[benzofuran-2,4′-piperidine] Building Block
Matthew M. Pompeo,
Sean M. Kelly,
Frédéric St-Jean
et al.
Abstract:An
efficient and scalable route to tert-butyl
3-oxo-3H-spiro[benzofuran-2,4′-piperidine]-1′-carboxylate,
a central prochiral intermediate in the synthesis of SHP2 inhibitor GDC-1971 (migoprotafib), was achieved. Preparation
of the title compound from readily available 2-fluorobenzaldehyde
included formation of a modified Katritzky benzotriazole hemiaminal,
which, upon deprotonation by n-butyllithium, participated
in umpolung reactivity via 1,2-addition to tert-butyl
4-oxopiperidine-1-carboxylate (N-Boc-4-piper… Show more
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