|
NISCAIR ONLINE PERIODICALS REPOSITORY (NOPR) >
NISCAIR PUBLICATIONS >
Research Journals >
Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.50B [2011] >
IJC-B Vol.50B(12) December 2011] >
| 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 |
| CC License: |  CC Attribution-Noncommercial-No Derivative Works 2.5 India |
| ISSN: | 0975-0983(Online); 0376-4699(Print) |
| Source: | IJC-B Vol.50B(12) December 2011]
|
|
