A one-pot reductive amination of aldehydes and ketones with NaBH4 was developed with a view to providing efficient, economical and greener synthetic conditions. A recyclable iron-based Lewis catalyst, Aquivion-Fe, was used to promote imine formation in cyclopentyl methyl ether, followed by the addition of a small amount of methanol to the reaction mixture to enable C=N reduction by NaBH4. The protocol, applied to a wide number of amines and carbonyl compounds, resulted in ever complete conversion of these latter with excellent chemoselectivity towards the expected amination products in the most cases. Isolated yields, determined for a selection of the screened substrates, were found consistent with the previously obtained conversion and selectivity data. Cinacalcet, an important active pharmaceutical ingredient, was efficiently prepared by the title procedure.

Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride / V. Airoldi, O. Piccolo, G. Roda, R. Appiani, F. Bavo, R. Tassini, S. Paganelli, S. Arnoldi, M. Pallavicini, C. Bolchi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - 2020:2(2020 Jan 16), pp. 162-168. [10.1002/ejoc.201901614]

Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride

G. Roda;R. Appiani;F. Bavo;S. Arnoldi;M. Pallavicini
Penultimo
;
C. Bolchi
Ultimo
2020

Abstract

A one-pot reductive amination of aldehydes and ketones with NaBH4 was developed with a view to providing efficient, economical and greener synthetic conditions. A recyclable iron-based Lewis catalyst, Aquivion-Fe, was used to promote imine formation in cyclopentyl methyl ether, followed by the addition of a small amount of methanol to the reaction mixture to enable C=N reduction by NaBH4. The protocol, applied to a wide number of amines and carbonyl compounds, resulted in ever complete conversion of these latter with excellent chemoselectivity towards the expected amination products in the most cases. Isolated yields, determined for a selection of the screened substrates, were found consistent with the previously obtained conversion and selectivity data. Cinacalcet, an important active pharmaceutical ingredient, was efficiently prepared by the title procedure.
Amination; Aquivion; Chemoselectivity; Cinacalcet; Sodium borohydride
Settore CHIM/06 - Chimica Organica
Settore CHIM/08 - Chimica Farmaceutica
16-gen-2020
7-nov-2019
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/722642
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