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US 7,465,830 B2Granted
Method of preparing pseudonorephedrine
AssigneeIllinois State University
InventorsShawn R. Hitchcock, Jonathan Andrew Groeper
Life of this patent
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Abstract
A method of making high diastereoselective and enantiomerically pure pseudonorephedrine and the hitherto unknown compound (1R,2R) pseudonorephedrine.
Claims22
A method of making (1S,2S) pseudonorephedrine comprising:
- A) providing (1R,2S) norephedrine as a starting material;
- B) acylating the amine to produce
- as a secondary carbamate derivative;
- C) treating the secondary carbamate derivative to displace the alcohol and invert the phenyl group to produce the oxazolidinones
- as a major product, and
- as a minor product;
- and
- D) hydrolyzing the major product oxazolidinone to form (1S,2S) pseudonorephedrine.
5 more elements
A method of making (1R,2R) pseudonorephedrine comprising:
- A) providing (1S,2R) norephedrine as a starting material;
- B) acylating the amine to produce
- as a secondary carbamate derivative;
- C) treating the secondary carbamate derivative to displace the alcohol and invert the phenyl group to produce the oxazolidinones
- as a major product;
- and
- as a minor product;
- and
- D) hydrolyzing the major product oxazolidinone to form (1R,2R) pseudonorephedrine.
6 more elements
Dependencies are inferred from the claim text.