Selective alkylation of an alcohol substituted phenol compound
AssigneeAbbott Laboratories
InventorsXiu C. Wang, Ashok V. Bhatia, Steven Chamberlin, Luping Liu
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Abstract
The present invention relates to a process for the selective alkylation of intermediates of betaxolol.
Claims25
A process for the selective alkylation of an alcohol functionality on an alcohol substituted phenol compound comprising reacting an alkylating agent with said alcohol substituted phenol compound in the presence of a strong base and a solvent.
A process for the production of 4-(2-Cyclopropylmethoxy)-ethyl!-phenol comprising reacting 4-Hydroxyphenethanol with an alkyating agent in the presence of a strong base and a solvent to produce 4-(2-Cyclopropylmethoxy)-ethyl!-phenol.
A process for the production of Betaxolol comprising the steps of:
- a) reacting 4-Hydroxyphenethanol with (Chloromethyl)cyclopropane or (Bromomethyl)cyclopropane in the presence of a strong base and a solvent to produce 4-(2-Cyclopropylmethoxy)-ethyl!-phenol;
- b) reaction 4-(2-Cyclopropylmethoxy)-ethyl!-phenol with epichlorohydrin in presence of base to form 1- {4-2-(Cyclopropylmethoxy)-ethyl!-phenoxy}-2,3-epoxypropane;
- and
- c) reacting 1-{4-2-(Cyclopropylmethoxy)ethyl!phenoxy}-2,3-epoxypropane with isopropylamine to produce Betaxolol.
A process for the production of Betaxolol hydrochloride comprising the steps of:
- a) reacting 4-Hydroxyphenethanol with (Chloromethyl)cyclopropane or (Bromomethyl)cyclopropane in the presence of a strong base and a solvent to produce 4-(2-Cyclopropylmethoxy)-ethyl!-phenol;
- b) reaction 4-(2-Cyclopropylmethoxy)-ethyl!-phenol with epichlorohydrin in presence of base to form 1-{4-2-(Cyclopropylmethoxy)-ethyl!-phenoxy}-2,3-epoxypropane;
- c) reacting 1-{4-2-(Cyclopropylmethoxy)ethyl!phenoxy}-2,3-epoxypropane with isopropylamine to produce Betaxolol;
- and
- d) forming the hydrochloride salt form of betaxolol by addition of HCl.
Dependencies are inferred from the claim text.