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
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 opti...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | deu |
| Published: |
Swiss Chemical Society
2006-09-01
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| Series: | CHIMIA |
| Subjects: | |
| Online Access: | https://chimia.ch/chimia/article/view/4212 |
| Summary: | 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.
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| ISSN: | 0009-4293 2673-2424 |