Optically active 4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten

Details Optically active 4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten Optically active 4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten

1980-06-18

1983-05-24

Trousof, Natalie

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

424306, 560 84, 560124, 568346, 568356, C07C 49537

Patent

active

043851860

ABSTRACT:
The present invention relates to a method for producing an optically active (+)-(s)-4-hydroxy-3-methyl-2-2'-propynyl-2-cyclopentenone which comprises reacting (.+-.)-4-hydroxy-3-methyl-2-2'-propynyl-2-cyclopentenone acid phthalate of the formula (II), ##STR1## with an optically active (+)-.alpha.-phenyl-.beta.-p-tolylethylamine to produce diastereomer salts, separating an optically active (-)-4-hydroxy-3-methyl-2-2'-propynyl-2-cyclopentenone acid phthalate by making use of a solubility difference between the diastereomer salts, and then hydrolyzing said optically active acid phthalate in water or a solvent containing water in the presence or absence of a base below the small excess of the stoichiometric amount, and novel (.+-.)-4-hydroxy-3-methyl-2-2'-propynyl-2-cyclopentenone acid phthalate and its production.

REFERENCES:
patent: 3931291 (1976-01-01), Horiuchi
patent: 4206151 (1980-06-01), Grudzinskas
patent: 4217251 (1980-08-01), Dastur

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