Efficient diastereoselective synthesis of cis-2-amino-1-indanol derivatives and cis- and trans-1-amino-2-indanol via Pd-catalyzed hydrogenation

Abstract

(±)-cis-2-amino-1-indanol was diastereoselectively synthesized from 1,2-indanedion-2-oxime in ethanol at 25 °C under 10% Pd/C-catalyzed hydrogenation conditions. Under the same hydrogenation condition, 1,2-indanedion-2-oxime and their derivatives having one and/or two electron-donating groups in aliphatic or aromatic part of indanyl ring were diastereoselectively reduced to racemic cis-2-amino-1-indanol derivatives. From 1,2-indanedion-1-oxime, (±)-trans-1-amino-2-indanol was obtained in ethanol at 25 °C over a 10% Pd/BaSO₄ catalyst. In contrast, the 10% Pd/BaSO₄-catalyzed hydrogenation reaction in ethanol at 45 °C afforded cis-1-hydroxyamino-2-indanol from 1,2-indanedion-1-oxime, followed by reduction to form (±)-cis-1-amino-2-indanol. The diastereoselectivity of β-aminoindanols was dependent on the Pd catalyst, reaction temperature, and pH of the reaction medium.

Graphical Abstract

Keywords:

• β-Aminoindanol
• diastereoselective
• Pd-catalyzed hydrogenation

Acknowledgment

We would like to thank Editage (www.editage.co.kr) for English language editing.

Additional information

Funding

This research was supported by the Daegu Catholic University.