Process for preparing quinuclidine enantiomers

Details Process for preparing quinuclidine enantiomers Process for preparing quinuclidine enantiomers

1975-04-18

1976-12-14

Trousof, Natalie

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424267, C07D21142

Patent

active

039975436

ABSTRACT:
A new composition of matter, (+) 3-acetoxy- quinuclidine and its salts, ophthalmic compositions comprising this compound or any of its physiologically acceptable salts in a suitable carrier such as a phosphate buffer, and a process of preparation of the active ingredients, which comprises esterifying quinuclidinol so as to obtain racemic 3-lower-alkoxy quinuclidine, subjecting same to enzymatic hydrolysis by a cholinesterase so as to selectively hydrolyze the (-) isomer, separating the unchanged (+) lower-alkoxy quinuclidine, hydrolyzing the latter and esterifying it to the desired compound. Amongst various homolophes the preferred compound is (+)3-acetoxy quinuclidine as this is pharmaceutically the most potent one.

REFERENCES:
kamilov, et al., Chem. Abst. 67: 10310y (1967).
Lieberman, et al., Chem. Abst. 67: 98897d (1967).
Ferlux, Fr. U. 5042, Chem. Abst. 71: 79711e (1969).
Agugini, et al., Chem. Abst. 70: 27540h (1969).
Karrer, Org. Chem. 2nd Ed. (1946) pp. 92-102.

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