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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]

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