Malaysian Journal of Analytical Sciences Vol 21 No 5 (2017): 1176 - 1182

DOI: https://doi.org/10.17576/mjas-2017-2105-22

 

 

 

STEREOSELECTIVE REDUCTION OF 1-BENZYL-3,3-DIMETHYL-5-METHYLENEPYRROLIDINE-2,4-DIONE USING SODIUM BOROHYDRIDE WITH SELECTED METAL CHLORIDES

 

(Tindak Balas Penurunan Stereoselektif 1-Benzil-3,3-Dimetil-5-Metilenapirolidina-2,4-Dion Menggunakan Natrium Borohidrat Dengan Logam Klorida Terpilih)

 

Nor Saliyana Jumali¹*, Zurina Shaameri², Habsah Mohamad³, Ahmad Sazali Hamzah²

 

¹Department of Chemistry, Kulliyyah of Science

International Islamic Universiti Malaysia, 25200 Indera Mahkota, Kuantan, Malaysia

²Institute of Science

Universiti Teknologi Mara, 40450 Shah Alam, Selangor, Malaysia

³Institute of Marine Biotechnology

Universiti Malaysia Terengganu, 21030 Kuala Nerus, Terengganu, Malaysia

 

*Corresponding author:  norsaliyana@iium.edu.my

 

 

Received: 21 August 2016; Accepted: 27 July 2017

 

 

Abstract

1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione is an intermediate product produced in the synthesis towards the natural bioactive compound, zopfiellamide A. This compound was synthesized via four main steps including dimethylations, addition with CuBr₂, cyclization with benzylamine and reaction with formaldehyde. The corresponding  intermediate was an α,ß-unsaturated ketone having exo-alkene group, and it was subjected to reduction using sodium borohydride and selected metal chlorides. In this study, the effect and the hydride transfer mechanism of sodium borohydride-metal chlorides system in the reduction of 1-benzyl-3,3-dimethyl-5-methylenepyrrolidine-2,4-dione was investigated based on the stereochemical outcome of the product.

 

Keywords:  stereoselective, reduction, metal borohydride, exo-alkene

 

Abstrak

1-benzil-3,3-dimetil-5-metilenapirolidina-2,4-dion ialah produk perantara yang terhasil di dalam sintesis terhadap sebatian aktif semulajadi, zopfiellamide A. Sebatian ini telah disintesis melalui empat langkah utama termasuklah metilasi berganda, penambahan kepada kuprum bromida, pengkitaran dengan benzilamina dan tindak balas dengan formaldehid. Sebatian perantara ini merupakan keton α,ß-tidaktepu yang mempunyai  kumpulan ekso-alkena, dan ia telah didedahkan kepada penurunan menggunakan natrium borohidrida dan logam klorida terpilih. Di dalam kajian ini, kesan dan mekanisma perpindahan hidrida oleh sistem natrium borohidrida-logam klorida di dalam menurunkan 1-benzil-3,3-dimetil-5-metilenapirolidina-2,4-dion telah dikaji berdasarkan stereokimia produk yang terhasil.

 

Kata kunci:  stereoselektif, penurunan, logam borohidrida, ekso-alkena

 

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