Synthesis of PEG-Functionalized Amines Using Ruthenium-Catalyzed Hydrogen Borrowing.

Autor: Rossi FV; School of Science and Technology, Chemistry Division, University of Camerino, via S. Agostino 1, I-62032 Camerino, MC, Italy., Starr JT; Pfizer Worldwide R&D, Eastern Point Road, Groton, Connecticut 06340, United States., Uccello DP; Pfizer Worldwide R&D, Eastern Point Road, Groton, Connecticut 06340, United States., Young JA; Pfizer Worldwide R&D, Eastern Point Road, Groton, Connecticut 06340, United States.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2020 Aug 07; Vol. 22 (15), pp. 5890-5894. Date of Electronic Publication: 2020 Jul 24.
DOI: 10.1021/acs.orglett.0c01965
Abstrakt: The polyethylene glycol (PEG) moiety has become increasingly important in medicinal chemistry. Herein, we describe the PEG functionalization of amines via hydrogen borrowing reductive amination. This was accomplished using the [Ru( p -cymene)Cl 2 ] 2 catalyst and phosphorus-containing ligand dppf or DPE to yield a variety of PEGylated primary and secondary amine products. Furthermore, we illustrate the utility of this method with the synthesis of quetiapine (Seroquel) in 62% isolated yield.
Databáze: MEDLINE
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