General Synthesis of 3-Azabicyclo[3.1.1]heptanes and Evaluation of Their Properties as Saturated Isosteres

Dmitry Dibchak,Mariya Snisarenko,Artem Mishuk,Oleh Shablykin, Lina Bortnichuk,Oleksii Klymenko-Ulianov, Yurii Kheylik,Iryna V. V. Sadkova,Henry S. S. Rzepa,Pavel K. K. Mykhailiuk

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION（2023）

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摘要

A general approach to 3-azabicyclo[3.1.1]heptanes by reduction of spirocyclic oxetanyl nitriles was developed. The mechanism, scope, and scalability of this transformation were studied. The core was incorporated into the structure of the antihistamine drug Rupatidine instead of the pyridine ring, which led to a dramatic improvement in physicochemical properties.

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关键词

Bicyclo[1,1,1]Pentane,Bicyclo[3,1]Heptane,Isosteres,Oxetanes,Spirocycles

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