Continuous flow Aza-Michael reaction for preparing the fast-acting synthetic opioid drug Remifentanil
Abstract Remifentanil is a modern fentanyl analogue with ultrashort-action granted by an esterase-labile methyl propanoate chain. Here, we present the development of a continuous flow methodology for the key N-alkylation step of remifentanil preparation in a biphasic, "slug-flow" regime. W...
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| Main Authors: | , , |
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| Format: | Book |
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Universidade de São Paulo,
2023-06-01T00:00:00Z.
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| Summary: | Abstract Remifentanil is a modern fentanyl analogue with ultrashort-action granted by an esterase-labile methyl propanoate chain. Here, we present the development of a continuous flow methodology for the key N-alkylation step of remifentanil preparation in a biphasic, "slug-flow" regime. We screened parameters under microwave-assisted reactions, translated conditions to flow settings, and obtained remifentanil under 15-min residence time in a 1-mL microreactor, with a space-time yield of 89 mg/mL·h and 94% yield. |
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| Item Description: | 2175-9790 10.1590/s2175-97902023e22764 |