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: (2S)-(+)-3-Chloropropane-1,2-diol, is researched, Molecular C3H7ClO2, CAS is 60827-45-4, about Asymmetric synthesis of (S)-Metoprolol.COA of Formula: C3H7ClO2.
Enantioenriched (S)-3-chloro-1,2-propanediol and (R)-epichlorohydrin were obtained by a kinetic hydrolysis resolution of racemic epichlorohydrin using (S,S)-salen-cobalt acetate and the synthesis of the target compound [i.e., 99% optically pure (S)-Metoprolol] was achieved by a reaction of 4-(2-methoxyethyl)phenol with (2S)-3-chloro-1,2-propanediol and a subsequent amination with 2-propanamine. When (R)-epichlorohydrin was used as a chiral precursor, (S)-Metoprolol was also formed but less optically pure (>92%). The overall product yield 53.9% and the product thus [(-)-Metoprolol, (2S)-1-[4-(2-methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]-2-propanol] was confirmed by IR, 1H-NMR, 13C-NMR, MS. This method may be suitable for industrial process adaptation.
Compound(60827-45-4)COA of Formula: C3H7ClO2 received a lot of attention, and I have introduced some compounds in other articles, similar to this compound((2S)-(+)-3-Chloropropane-1,2-diol), if you are interested, you can check out my other related articles.
Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com