Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: (S)-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-methylamine, is researched, Molecular C6H13NO2, CAS is 82954-65-2, about Direct conversion of (R)-epichlorohydrin to (S)-3-aminopropane-1,2-diol: an important chiral C-3 building block.Safety of (S)-(2,2-dimethyl-[1,3]-dioxolan-4-yl)-methylamine.
A new and effective method for the preparation of (S)-3-amino-1,2-propanediol was established starting from (R)-epichlorohydrin. The synthetic approach involves the reaction of (R)-epichlorohydrin with acetone catalyzed by BF3·OEt2 to give (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane. Subsequent replacement of the Cl with NH2 group by azidation followed by reduction gave ((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methanamine, which was converted into (S)-3-aminopropane-1,2-diol·HCl by acetal deprotection with MeOH·HCl.
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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics