Preparation of gabapentin enacarbil intermediate
AssigneeTeva Pharmaceutical Industries Ltd.
InventorsElena BEN MOHA-LERMAN, Anna BALANOV, Miri ADLER
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Abstract
Allyl 1 {[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetate can be prepared by combining allyl 1-aminomethyl-1-cyclohexane acetate hydrochloride, a polar organic solvent, chloroethyl chloroformate, and an amine base or an inorganic base selected from a group consisting of carbonate and bicarbonate to provide a reaction mixture; and adding isobutyric acid to the reaction mixture. The product can be purified and/or converted to gabapentin enacarbil.
Claims33
A one-pot process for preparing allyl 1 {[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetate (compound 4) comprising:
- combining allyl 1-aminomethyl-1-cyclohexane acetate hydrochloride (compound 2), a polar organic solvent, chloroethyl chloroformate (“CEC”), and an amine base or an inorganic base selected from a group consisting of:
- carbonate and bicarbonate to provide a reaction mixture;
- and adding isobutyric acid to the reaction mixture to obtain allyl 1 {[α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetate (compound 4).
A process for recovering and purifying allyl 1 {[α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetate (compound 4) comprising:
- extracting a reaction mixture containing allyl 1 {[α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetate (compound 4) with a C5-C10 alkane;
- and removing the C5-C10 alkane to obtain purified allyl 1 {[α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetate (compound 4).
-46. (canceled)
Dependencies are inferred from the claim text.