3772-26-7Relevant articles and documents
Bio-based N-alkyl-2-pyrrolidones by Pd-catalyzed reductive N-alkylation and decarboxylation of glutamic acid
De Schouwer, Free,Adriaansen, Sander,Claes, Laurens,De Vos, Dirk E.
, p. 4919 - 4929 (2017/10/19)
Environmental regulations boost the search for new safer and less toxic bio-based solvents to replace controversial high-boiling solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide in the chemical industry. Recently, N-alkyl-2-pyrrolidones and 5-methyl-N-alkyl-2-pyrrolidones were proposed as attractive alternative solvents for many applications. Here, we report a bio-based two-step chemocatalytic system for the synthesis of a broad range of N-alkyl-2-pyrrolidones starting from glutamic acid and C3-C5 carbonyl compounds. In the first step N-mono-alkylated derivatives of glutamic acid were synthesized in high yields (>85%) by a mild and efficient Pd-catalyzed reductive N-alkylation. Subsequently, thermally induced lactamization to the corresponding N-alkylpyroglutamic acid followed by Pd-catalyzed decarboxylation at 250 °C under inert atmosphere resulted in N-alkyl-2-pyrrolidones. Hydrolytic degradation was partially counteracted by the neutralization of the N-alkylpyroglutamic acid substrate with a base, resulting in yields up to 82%. Finally, both reaction steps were successfully combined in a one-pot process using the same Pd/Al2O3 catalyst in different conditions of gas atmosphere and temperature.
Tandem catalysis: The sequential mediation of olefin metathesis, hydrogenation, and hydrogen transfer with single-component Ru complexes
Louie,Bielawski,Grubbs
, p. 11312 - 11313 (2007/10/03)
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Extension of the Eschweiler-Clarke procedure to the N-alkylation of amides
Fache, Fabienne,Jacquot, Laurent,Lemaire, Marc
, p. 3313 - 3314 (2007/10/02)
The selective N-alkylation of amides (cyclic or acyclic) under hydrogen is reported using aldehydes or ketones as alkylating agents and Pd/C/Na2SO4 as catalyst. Good isolated yields are obtained (81% to 98%).
