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US 8,148,528 B2Granted
Processes and compounds for the preparation of normorphinans
AssigneeMallinckrodt Inc.
InventorsPeter X. Wang, Frank W. Moser, Gary L. Cantrell, Tao Jiang, Robert E. Halvachs, Christopher W. Grote
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Abstract
The invention generally provides processes and intermediate compounds useful for the production of normorphinans and derivatives of normorphinans.
Claims17
A compound comprising of Formula 21a:
- wherein:
- R1 and R2 are independently chosen from hydrogen, OH, NH2, SH, CF3, hydrocarbyl, substituted hydrocarbyl, alkyl ketal, alkyl thiol ketal, and alkyl dithiol ketal, wherein when R1 and R2 are different they form an epimeric pair, and wherein R1 and R2 together may form a group chosen from =0, ═S, cycloalkyl ketal, cycloalkyl thiol ketal, and cycloalkyl dithiol ketal;
- R3 is chosen from hydrogen, halogen, OH, NH2, CN, CF3, SO2R8, hydrocarbyl, and substituted hydrocarbyl;
- R4 and R5 are independently chosen from —(CH2)nCH3 and CH3;
- R8 is chosen from hydrocarbyl and substituted hydrocarbyl;
- X is halogen;
- Y is chosen from a benzyloxycarbonyl group, an alkylamidocarbonyl group, a trialkylsilyl group, an alkylsulfonyl group, and an aryl sulfonyl group;
- and
- n is an integer from 1 to 8.
6 more elements
A process for the preparation of compound 21a, the process comprising the following reaction scheme:
- wherein:
- R1 and R2 are independently chosen from hydrogen, OH, NH2, SH, CF3, hydrocarbyl, substituted hydrocarbyl, alkyl ketal, alkyl thiol ketal, and alkyl dithiol ketal, wherein when R1 and R2 are different they form an epimeric pair, and wherein R1 and R2 together may form a group chosen from =0, ═S cycloalkyl ketal, cycloalkyl thiol ketal, and cycloalkyl dithiol ketal;
- R3 is chosen from hydrogen, halogen, OH, NH2, CN, CF3, SO2R8, hydrocarbyl, and substituted hydrocarbyl;
- R4 and R5 are independently chosen from —(CH2)nCH3, and CH3;
- R8 is chosen from hydrocarbyl and substituted hydrocarbyl;
- X and X1 are independently halogen;
- Y is chosen from a benzyloxycarbonyl group, an alkylamidocarbonyl group, a trialkylsilyl group, an alkylsulfonyl group, and an aryl sulfonyl group;
- m is an integer from 1 to 3;
- and
- n is an integer from 1 to 8.
7 more elements
Dependencies are inferred from the claim text.