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American Chemical Society, Organic Process Research and Development, 5(16), p. 798-810, 2012

DOI: 10.1021/op300084z

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A Flow-Based Synthesis of 2-Aminoadamantane-2-carboxylic Acid

This paper is available in a repository.
This paper is available in a repository.

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Abstract

The development of a new, high-yielding, scalable and safe process for the preparation of 2-aminoadamantane-2-carboxylic acid (1) is described. This geminal, functionalized achiral amino acid has been reported to possess interesting biological activity as a transport mediator due to its unique physiochemical properties. We report herein on the use of various mesoreactor flow devices to expedite the lab-scale synthesis of this molecule by simplifying the processing requirements for use of several potentially hazardous reagent combinations and reaction conditions.