One pot synthesis of bridgehead amino alcohols from diamantoid hydrocarbons

Abstract

An efficient approach for the synthesis of amino alcohols directly from cage hydrocarbons has been developed. Multigram scalability, good yields and one-pot procedure, that utilize readily available reagents along with synthetic convenience showed its usefulness. The proposed one-pot method includes sequential reactions of cage hydrocarbon with nitric acid, further amination of intermediate nitroxy derivative with urea, followed by oxidation of previously generated amine to amino alcohol on addition of conc. H₂SO₄.

Graphical Abstract

Keywords:

• Amination
• amino alcohols
• cage hydrocarbons
• one-pot method
• oxidation

Additional information

Funding

This publication was supported by the Russian Science Foundation (Grant No. 21-73-20103) (¹³C NMR spectra were recorded with the help of Collective Usage Center "New Materials and Resource-saving Technologies," Lobachevsky State University of Nizhny Novgorod) and the other spectral data was achieved under the framework of the Project part of the State Assignment 075-03-2023-213, project FSSE-2023-0003 with Ministry of Education and Science of Russian Federation.