Thursday 26 June 2014

Acid-Facilitated Debenzylation of N-Boc, N-Benzyl Double Protected 2-Aminopyridinomethylpyrrolidine Derivatives

Tetrahedron. Author manuscript; available in PMC Feb 4, 2013.
Published in final edited form as:
PMCID: PMC3358821
NIHMSID: NIHMS344972

Acid-Facilitated Debenzylation of N-Boc, N-Benzyl Double Protected 2-Aminopyridinomethylpyrrolidine Derivatives

Abstract

2-Aminopyridinomethyl pyrrolidines represent a class of highly potent and selective neuronal nitric oxide synthase inhibitors. Conditions for a Mitsunobu reaction of a naphthol and a hindered secondary alcohol were optimized to give good to excellent yields. A key step in the synthesis of these inhibitors is the deprotection of the benzyl group from the N-Boc and N-Bn double protected 2-aminopyridine ring at a late stage of the synthesis, which has been proven difficult in our previous syntheses. Acetic acid was found to facilitate the N-Bn deprotection.
Keywords: 2-Aminopyridinomethyl pyrrolidines, Mitsunobu reaction, N-Benzyl deprotection, Palladium-catalyzed hydrogenation

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Monday 16 June 2014

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Wednesday 11 June 2014

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