Optically active propargyl alcohol derivative and a method for preparation of the same

A method for the preparation of optically active propargyl alcohol derivatives of the formula (I):

• ##STR31## wherein X represents a member selected from the group consisting of phenyl and thienyl radicals and R represents a member selected from the group consisting of lower alkyl radicals, halogenated methyl radicals, a phenyl radical and substituted phenyl radicals each having at least one substituent selected from the group consisting of lower alkyl radicals and halogen atoms, which method comprises the steps of:
• bringing a racemic modification of l- and d-propargyl alcohol derivatives of the formula (I) into contact with l-brucine in an organic solvent, whereby a mixture of diastereomers of L-brucine with an l-isomer and a d-isomer of a propargyl alcohol derivative of the formula (I) is produced and one of said diastereomers deposits from said organic solvent
• and the other one is dissolved in said organic solvent;
• separating said deposited diastereomer from the solution containing the other diastereomer;
• decomposing each of said diastereomers to dissociate l-brucine frorm the corresponding optically active isomer of the propargyl alcohol derivative of the formula (I) in the presence of an organic solvent which is capable of dissolving said corresponding optically active isomer and is incompatible with water by bringing each diastereomer into contact with an aqueous solution of a mineral acid;
• whereby the resulting optically active isomer is dissolved in the water-incompatible organic solvent and the dissociated l-brucine is dissolved in the aqueous mineral acid solution;
• and
• isolating the resultant optically active isomer from the decomposition mixture.