ChemInform Abstract: Large Scale Synthesis of N-Benzyl-4-formylpiperidine Through Partial Reduction of Esters Using Aluminum Hydride Reagents Modified with Pyrrolidine

Autor:	Kimio Hamamura, Shigeto Negi, Toyokazu Haga, Yukio Morita, Keizou Takayanagi, Taichi Abe
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Base (chemistry) Reducing agent Sodium Potassium chemistry.chemical_element General Medicine Aldehyde Combinatorial chemistry Pyrrolidine chemistry.chemical_compound chemistry Reagent Piperidine
Zdroj:	ChemInform. 32
ISSN:	1522-2667 0931-7597
Popis:	The modification of sodium bis(2-methoxyethoxy)aluminum hydride (SMEAH) with pyrrolidine provided a highly selective reducing agent to transform N -benzyl-4-ethoxycarbonylpiperidine into N -benzyl-4-formylpiperidine 1 under mild conditions. However, this simple modification led to a significant amount of N -benzyl-4-(pyrrolidin-1-ylmethyl)piperidine 4 due to overreduction of an intermediate. Our extensive research revealed that an alkaline base such as potassium tert -butoxide could suppress the formation of the by-product to give the desired aldehyde, enabling us to establish a viable synthetic process for a key intermediate of donepezil hydrochloride. The potential applications of this reagent are also described.
Databáze:	OpenAIRE
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