Efficient One‐Pot Reductive Aminations of Carbonyl Compounds with Aquivion‐Fe as a Recyclable Catalyst and Sodium Borohydride. Issue 2 (11th December 2019)

• Record Type: Journal Article
• Authors: Airoldi, Veronica; Piccolo, Oreste; Roda, Gabriella; Appiani, Rebecca; Bavo, Francesco; Tassini, Riccardo; Paganelli, Stefano; Arnoldi, Sebastiano; Pallavicini, Marco; Bolchi, Cristiano
• Is Part Of: European journal of organic chemistry. Issue 2(2020)
• Page Start: 162
• Page End: 168
• Publication Date: 2019-12-11
• Subjects: Amination -- Aquivion -- Chemoselectivity -- Cinacalcet -- Sodium borohydride; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201901614
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : Aldehydes and ketones were reductively aminated by a one‐pot procedure using a recyclable iron‐based Lewis catalyst, Aquivion‐Fe, to promote imine formation, and NaBH4 as reductant in cyclopentyl methyl ether and methanol. The developed protocol was successfully applied to the preparation of Cinacalcet, an important active pharmaceutical ingredient.