Back to results
US 12,297,195 B2Granted
Synthetic route to scopolamine and/or atropine
AssigneeSouthwest Research Institute
InventorsShawn T. Blumberg, Paul W. Miguel, Daniel A. Hinojosa
Life of this patent
Estimating the term…
Abstract
A synthetic route to scopolamine and/or atropine. In such context, the present invention identifies a method for preparing 6,7-dehydro atropine, which can be converted into either scopolamine and/or atropine, along with a method for converting a protected pyrrole into a tetrachlorobicylic compound, such as benzyl 3-oxo-8-azabicyclo[3.2.1]oct-6-ene-8-carboxylate.
Claims4
A method for preparing 6,7-dehydro atropine comprising:
- (a) providing a protected pyrrole having the following formula:
- wherein R may be an alkyl group, phenyl group, or benzyl group;
- (b) reacting the protected pyrrole with pentachloroacetone and forming a first tetrachloro-bicyclic compound having the following formula:
- wherein R may be an alkyl group, phenyl group, or benzyl group;
- (c) carrying out a reductive dechlorination of said first tetrachloro-bicyclic compound and forming a second bicyclic compound having the following formula:
- wherein R may be an alkyl group, phenyl group, or benzyl group;
- (d) carrying out a reductive methylation of the second bicyclic compound formed in step (c) and forming 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol having the following formula:
- (e) converting 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol into 6,7-dehydro tropine tosylate having the following formula:
- wherein −OTs is reference to −OSO2—Ar—CH3.
6 more elements
Dependencies are inferred from the claim text.