A short synthesis of 4-Hydroxypyrrolidine-2-One from Tetramic Acid Intermediates / Sharifah Nurin Zafirah, Noor Hidayah Pungot and Zurina Shaameri
4-Hydroxypyrrolidine-2-one 1 is useful as intermediates for synthesising antibiotic and antidepressant agents. Nevertheless, most organic synthesis routes are long and require a long time to generate the desired compounds, consisting of two reactions steps. The first step involves synthesising pyrro...
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Format: | Article |
Language: | English |
Published: |
2022.
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Online Access: | Get fulltext View Fulltext in UiTM IR |
LEADER | 02294 am a22002173u 4500 | ||
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001 | 60137 | ||
042 | |a dc | ||
100 | 1 | 0 | |a Zafirah, Sharifah Nurin |e author |
700 | 1 | 0 | |a Pungot, Noor Hidayah |e author |
700 | 1 | 0 | |a Shaameri, Zurina |e author |
245 | 0 | 0 | |a A short synthesis of 4-Hydroxypyrrolidine-2-One from Tetramic Acid Intermediates / Sharifah Nurin Zafirah, Noor Hidayah Pungot and Zurina Shaameri |
260 | |c 2022. | ||
856 | |z Get fulltext |u https://ir.uitm.edu.my/id/eprint/60137/1/60137.pdf | ||
856 | |z View Fulltext in UiTM IR |u https://ir.uitm.edu.my/id/eprint/60137/ | ||
520 | |a 4-Hydroxypyrrolidine-2-one 1 is useful as intermediates for synthesising antibiotic and antidepressant agents. Nevertheless, most organic synthesis routes are long and require a long time to generate the desired compounds, consisting of two reactions steps. The first step involves synthesising pyrrolidine- 2,4-diones from N-Boc-amino acids via Meldrum's acid-mediated reaction and tetramic acid cyclisation. Generally, 1-(3-diemthylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) is employed as a carboxyl activating agent in the reaction due to easy access and cost. In the present study, the short synthesis of 4-hydroxy pyrrolidin-2-one utilising N-Boc-alanine 2 and N-Boc-valine 3 as the amino acid was determined to produce tetramic acids 4 and 5. The present study employed easily obtainable starting chemical compounds and was less costly to synthesise the 5-substituted pyrrolidine- 2,4-diones via Meldrum's acid-mediated reaction and tetramic acid cyclisation. The amino acids employed were also readily protected by the tert-butoxycarbonyl (Boc) group to prevent the acids from reacting with other compounds. Resultantly, compounds 4 and 5 were successfully synthesised with 22% and 10% yields, respectively. The tetramic acids were then subjected to regioselective reduction with sodium borohydride (NaBH4) as the reducing agent in methanol to acquire compounds 6 (9%) and 7 (6%). All synthesised compounds were purified by column chromatography and characterised using nuclear magnetic resonance (1H and 13C NMR) spectroscopy. | ||
546 | |a en | ||
650 | 0 | 4 | |a Laboratories. General works |
650 | 0 | 4 | |a Hydroxylation |
650 | 0 | 4 | |a Chemical elements |
650 | 0 | 4 | |a Acids and bases |
655 | 7 | |a Article |