An Improved Process for Repaglinide via an Efficient and One Pot Process of (1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butan-1-amine – A Useful Intermediate
| Autor: | Naveenkumar Kolla, Chandrashekar R. Elati, Pravinchandra J. Vankawala, Srinivas Gangula, Eswaraiah Sajja, Yerremilli Anjaneyulu, Apurba Bhattacharya, Venkataraman Sundaram, Vijayavitthal T. Mathad |
|---|---|
| Jazyk: | German<br />English<br />French |
| Rok vydání: | 2006 |
| Předmět: | |
| Zdroj: | CHIMIA, Vol 60, Iss 9 (2006) |
| Druh dokumentu: | article |
| ISSN: | 0009-4293 2673-2424 |
| DOI: | 10.2533/chimia.2006.593 |
| Popis: | The development of a large-scale synthesis for (1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butan-1-amine (S-(+)-1), a key intermediate of repaglinide (2), is described. The process conditions for S-(+)-1 involving nucleophilic substitution, Grignard reaction, reduction and resolution were optimized and telescoped. The racemization of the undesired enantiomer R-(?)-1 offers a distinctive advantage in terms of cost and overall yield over the existing process. This communication also describes the control of a DcU byproduct obtained during the condensation of S-(+)-1 with phenyl acetic acid derivative 3 in the synthesis of 2. |
| Databáze: | Directory of Open Access Journals |
| Externí odkaz: |
|