PURPOSE: To obtain the titled compound useful as an intermediate for acaricides in high stereoselectivity, by reacting an erythro-2-amino-1-(4-substituted phenyl)-1-chloropropane hydrochloride with carbonyl sulfide in an organic solvent in the presence of a deacidifying agent.
CONSTITUTION: An erythro compound of formula II (X is halogen or lower alkyl, particularly Cl or CH3) is reacted with sulfuric acid to give a compound of formula III, which is then subjected to the ring closure with an alkali to afford the trans compound of formula. IV. The resultant trans compound of formula IV is then reacted with hydrochloric acid to give an erythro compound of formula V, which is then reacted with carbonyl suflide in an organic solvent in the presence of a deacidifying agent, preferably triethylamine, to afford the trans compound of formulaI. According to the method, the trans compound of formula IV is obtained from both the threo and the erythro compounds of formula III, and the stereoselectivity is high due to almost no contamination of the stereoisomers in the subsequent steps. Therefore, this method is industrially advantageous.
MATSUI NOBUO
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