PURPOSE: To obtain the aimed product by reacting an optically active epichlorohydrin with an alcohol in the presence of an acidic catalyst to give an optically active glycerol derivative, reacting the resultant glycerol derivative with a sulfonyl halide and deprotecting the resultant sulfonate in the presence of an acidic catalyst, metallic catalyst, etc.
CONSTITUTION: (R)-Epichlorohydrin is reacted with an alcohol expressed by the formula R1OH (R1 is benzyl, CH2=CHCH2-, etc.) in the presence of an acidic catalyst (e.g., Lewis acid) at 30-80°C to give a compound expressed by formula I, which is then reacted with a sulfonyl halide (e.g., chloromethane sulfonic acid) at 0-70°C to afford a compound expressed by formula II. The compound expressed by formula II is reacted in the presence of an acidic catalyst (e.g., p-toluenesulfonic acid) and/or metallic catalyst (e.g., Pd) at 20-100°C to give a compound expressed by formula III, which is then subjected to intramolecular cyclization reaction to provide the (S)-bichlorohydrin.
SAKAGUCHI KAZUHIKO
KASAI NAOYA
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