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http://nopr.niscpr.res.in/handle/123456789/13222| Title: | Direct conversion of (R)-epichlorohydrin to (S)-3-aminopropane-1,2-diol: An important chiral C-3 building block |
| Authors: | Bhavani, Ch Babu, K Chandra Naresh, E Sridhar, P Madhusudhan, G |
| Keywords: | (S)-3-Aminopropane-1,2-diol;(R)-epichlorohydrin;Azidation;Rivaroxaban (Bay-59-7939); -amino alcohol |
| Issue Date: | Dec-2011 |
| Publisher: | NISCAIR-CSIR, India |
| Abstract: | A new and effective method for the preparation of optically active (S)-3-amino-1,2-propanediol 1 has been established starting from (R)-epichlorohydrin 2. The synthetic approach involves the reaction of (R)-epichlorohydrin 2 with acetone catalyzed by boron trifluoride etherate (BF3·OEt2) to give the (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane, 5. Replacing the chloro group in (R)-5 with amino group by azidation followed by reduction gives ((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methanamine 7. Acetal deprotection of the obtained (S)-7 with MeOH.HCl gives (S)-3-aminopropane-1,2-diol·HCl. |
| Page(s): | 1807-1811 |
| ISSN: | 0975-0983(Online); 0376-4699(Print) |
| Appears in Collections: | IJC-B Vol.50B(12) December 2011] |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| IJCB 50B(12) 1807-1811.pdf | 82.12 kB | Adobe PDF | View/Open |
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