One-Pot Synthesis of 1-[(1-Phenyl-1-Dialkoxyphosphoryl)-Methyl]-2- Pyrrolidinone

Petri   A.   Turhanen; Pasi      Soininen; Jouko   J.   Vepsalainen

doi:10.2174/1570178043400442

Abstract

A novel one-pot method to 1-[(1-phenyl-1-dialkoxyphosphoryl)-methyl]-2-pyrrolidinones (1a-c), where R=Me, Et, n-Hex, from the benzaldehyde (2), 4-aminobutyric acid (3) and dialkyl phosphite (4a-c) has been developed with reasonable 61-80% yields. Preparation of 4-{[(dimethoxyphosphoryl)-phenyl-methyl]- amino}-butyric acid (5) with high 85% yield is also described. Unexpected large 5JHP coupling constants 3.35, 3.37 and 3.15 Hz for compounds 1a-c, respectively, were observed.

Keywords: phosphorus, imine, pyrrolidinone, esters, coupling

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Letters in Organic Chemistry

Title: One-Pot Synthesis of 1-[(1-Phenyl-1-Dialkoxyphosphoryl)-Methyl]-2- Pyrrolidinone

Volume: 1 Issue: 4

Author(s): Petri A. Turhanen, Pasi Soininen and Jouko J. Vepsalainen

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Keywords: phosphorus, imine, pyrrolidinone, esters, coupling

Abstract: A novel one-pot method to 1-[(1-phenyl-1-dialkoxyphosphoryl)-methyl]-2-pyrrolidinones (1a-c), where R=Me, Et, n-Hex, from the benzaldehyde (2), 4-aminobutyric acid (3) and dialkyl phosphite (4a-c) has been developed with reasonable 61-80% yields. Preparation of 4-{[(dimethoxyphosphoryl)-phenyl-methyl]- amino}-butyric acid (5) with high 85% yield is also described. Unexpected large 5JHP coupling constants 3.35, 3.37 and 3.15 Hz for compounds 1a-c, respectively, were observed.

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Turhanen A. Petri, Soininen Pasi and Vepsalainen J. Jouko, One-Pot Synthesis of 1-[(1-Phenyl-1-Dialkoxyphosphoryl)-Methyl]-2- Pyrrolidinone, Letters in Organic Chemistry 2004; 1 (4) . https://dx.doi.org/10.2174/1570178043400442