Processes and compounds for the preparation of normorphinans

1. A compound comprising of Formula 21a:

wherein:

R 1 and R 2 are independently chosen from hydrogen, OH, NH 2 , SH, CF 3 , hydrocarbyl, substituted hydrocarbyl, alkyl ketal, alkyl thiol ketal, and alkyl dithiol ketal, wherein when R 1 and R 2 are different they form an epimeric pair, and wherein R 1 and R 2 together may form a group chosen from =0, ═S, cycloalkyl ketal, cycloalkyl thiol ketal, and cycloalkyl dithiol ketal;

R 3 is chosen from hydrogen, halogen, OH, NH 2 , CN, CF 3 , SO 2 R 8 , hydrocarbyl, and substituted hydrocarbyl;

R 4 and R 5 are independently chosen from —(CH 2 ) n CH 3 and CH 3 ;

R 8 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.

2. The compound of claim 1 , wherein:

R 1 , R 2 , and R 3 are each hydrogen;

R 4 and R 5 are each CH 3 ;

X is bromine; and

Y is chosen from —Si(CH 3 ) 3 , and —SO 2 CH 3 .

3. The compound of claim 1 , wherein the optical activity of the compound is (+) or (−), and the configuration of C-5, C-13, and C-9, respectively, of the compound may be RRR, RRS, RSR, RSS, SRR, SRS, SSR, or SSS, provided that the C-15 and the C-16 carbons are both either on the alpha face or the beta face of the molecule.

4. A process for the preparation of compound 21a, the process comprising the following reaction scheme:

wherein:

R 1 and R 2 are independently chosen from hydrogen, OH, NH 2 , SH, CF 3 , hydrocarbyl, substituted hydrocarbyl, alkyl ketal, alkyl thiol ketal, and alkyl dithiol ketal, wherein when R 1 and R 2 are different they form an epimeric pair, and wherein R 1 and R 2 together may form a group chosen from =0, ═S cycloalkyl ketal, cycloalkyl thiol ketal, and cycloalkyl dithiol ketal;

R 3 is chosen from hydrogen, halogen, OH, NH 2 , CN, CF 3 , SO 2 R 8 , hydrocarbyl, and substituted hydrocarbyl;

R 4 and R 5 are independently chosen from —(CH 2 ) n CH 3 , and CH 3 ;

R 8 is chosen from hydrocarbyl and substituted hydrocarbyl;

X and X 1 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.

5. The process of claim 4 , wherein:

YX is chosen from (CH 3 ) 3 SiCl, POCl 3 , and CH 3 SO 2 Cl;

R 1 , R 2 , and R 3 are each hydrogen;

R 4 and R 5 are each CH 3 ; and

X 1 is bromine.

6. The process of claim 4 , wherein the molar/molar ratio of compound 20 to YX is from about 1:1 to about 1:50, the reaction is conducted in the presence of an aprotic solvent, and the reaction is conducted at a temperature ranging from about 0° C. to about 80° C.

7. The process of claim 4 , wherein the yield of compound 21 is from about 60% to about 90%.

8. The compound of claim 1 wherein Y is a benzyloxycarbonyl group.

9. The compound of claim 1 wherein Y is an alkylamidocarbonyl group.

10. The compound of claim 1 wherein Y is a trialkylsilyl group.

11. The compound of claim 1 wherein Y is an alkylsulfonyl group.

12. The compound of claim 1 wherein Y is an aryl sulfonyl group.

13. The process of claim 4 wherein Y is a benzyloxycarbonyl group.

14. The process of claim 4 wherein Y is an alkylamidocarbonyl group.

15. The process of claim 4 wherein Y is a trialkylsilyl group.

16. The process of claim 4 wherein Y is an alkylsulfonyl group.

17. The process of claim 4 wherein Y is an aryl sulfonyl group.