Reivindicaciones
CLAIMS: 1. A method for determining the enantiomeric purity of a compound of formula (I): <img class="EMIRef" id="482902-imgf000021-0001" /> or a salt thereof, wherein Y is hydrogen or a substituent of the formula: <img class="EMIRef" id="482902-imgf000021-0002" /> comprising: a) preparing a sample comprising a compound of formula (I); b) introducing the sample to a chiral high performance liquid chromatography column comprising a stationary phase capable of separating enantiomers of the compound of formula (I), wherein the enantiomers of the compound of formula (I) are compounds of the formula (II) and (III) or salts thereof: <img class="EMIRef" id="482902-imgf000021-0003" /> c) eluting the sample from the column with a mobile phase using chromatographic conditions; d) identifying the respective retention times of the enantiomers of formula (II) and (III) or salts thereof; and e) comparing the areas of the peaks associated with the retention times of enantiomers (II) and (III), thereby quantifying the enantiomers, and thereby determining the enantiomeric purity of a compound of formula (I). 2. The method of claim 1 , wherein the salt of any of the compounds of formula I, formula II, or formula III is the hydrobromide or tartrate salt. 3. The method of claim 2, wherein Y is hydrogen. 4. The method of claim 2, wherein Y is a substituent of the formula: <img class="EMIRef" id="482902-imgf000022-0001" /> 5. The method of claim 3, wherein the compound of formula (I) is 2,2-diphenyl- 2-(pyrrolidin-3-yl)acetamide tartrate of the formula: <img class="EMIRef" id="482902-imgf000022-0002" /> 6. The method of claim 4, wherein the compound of formula (I) is 2- { 1 -[2-(2,3- dihydrobenzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide hydrobromide of the formula: <img class="EMIRef" id="482902-imgf000022-0003" /> 7. The method of claim 1, wherein the column comprises at least one polysaccharide as a stationary phase. 8. The method of claim 7, wherein the polysaccharide is selected from the group consisting of derivatized amylose, derivatized cellulose, and mixtures thereof. 9. The method of claim 1 , wherein the mobile phase comprises at least one solvent selected from the group consisting of non-polar solvents, polar aprotic solvents, polar protic solvents, and mixtures thereof. 10. The method of claim 9, wherein the solvent is selected from the group consisting of hexane, acetonitrile, isopropanol, water, and mixtures thereof. 11. The method of claim 10, wherein the mobile phase further comprises at least one additive. 12. The method of claim 11, wherein the additive is diethylamine. 13. The method of claim 11 , wherein the additive is a buffer. 14. The method of claim 13, wherein the buffer is a phosphate buffer. 15. The method of claim 3, wherein the chromatographic conditions are reverse- phase conditions. 16. The method of claim 15, wherein the stationary phase of the column comprises a derivatized cellulose and the mobile phase comprises acetonitrile, water, and phosphate buffer, and the pH of the mobile phase is about 2. 17. The method of claim 4, wherein the chromatographic conditions are normal- phase conditions. 18. The method of claim 17, wherein the stationary phase of the column comprises a derivatized amylose and the mobile phase comprises hexane, isopropanol, and diethylamine. 19. The compound (5)-2-{l-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]-3- pyrrolidinyl}-2,2-diphenylacetamide or salt thereof having less than about 0.5% by percentage area HPLC of (i?)-2-(l-(2-(2,3-dihydrobenzofuran-5-yl)ethyl)-3-pyrrolidinyl)-2,2- diphenylacetamide, as determined by the method of claim 4. 20. The (5)-2-{ l-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2- diphenylacetamide or salt thereof of claim 19 having less than about 0.1% by percentage area HPLC of(i?)-2-(l-(2-(2,3-dihydrobenzofuran-5-yl)ethyl)-3-pyrrolidinyl)-2,2- diphenylacetamide . 21. The (S)-2-{ l-[2-(2,3-dihydrobenzoflιran-5-yl)ethyl]-3-pyrrolidinyl}-2,2- diphenylacetamide or salt thereof of claim 20 having less than about 0.01% by percentage area HPLC of (7?)-2-(l-(2-(2,3-dihydrobenzofuran-5-yl)ethyl)-3-pyrrolidinyl)-2,2- diphenylacetamide . 22. The (S)-2-{ l-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2- diphenylacetamide or salt thereof of claim 19, wherein the (S)-2-{ l-[2-(2,3- dihydrobenzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide is (S)-2-{ l-[2-(2,3- dihydrobenzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide hydrobromide. 23. The (S)-2-{ l-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2- diphenylacetamide or salt thereof of claim 19, wherein the (5)-2-{l-[2-(2,3- dihydrobenzofiiran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide is (5)-2-{ l-[2-(2,3- dihydrobenzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide tartrate. 24. The compound 2,2-diphenyl-2-[(35)-pyrrolidin-3-yl]acetamide or salt thereof having less than about 0.5% by percentage area HPLC of 2,2-diphenyl-2-[(3i?)-pyrrolidin-3- yljacetamide, as determined by the method of claim 3. 25. The compound 2,2-diphenyl-2-[(35)-pyrrolidin-3-yl]acetamide or salt thereof of claim 24 having less than about 0.1% by percentage area HPLC of 2,2-diphenyl-2-[(3i?)- pyrrolidin-3 -yl]acetamide. 26. The compound 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide or salt thereof of claim 25 having less than about 0.01% by percentage area HPLC of 2,2-diphenyl-2-[(3i?)- pyrrolidin-3-yl]acetamide. 27. The 2,2-diphenyl-2-[(3iS)-pyrrolidin-3-yl]acetamide or salt thereof of claim 24, wherein the 2,2-diphenyl-2-[(35)-pyrrolidin-3-yl]acetamide is 2,2-diphenyl-2-[(35)- pyrrolidin-3-yl]acetamide tartrate. 28. A process for preparing (S)-2-{ 1 -[2-(2,3-dihydrobenzofuran-5-yl)ethyl]-3- pyrrolidinyl}-2,2-diphenylacetamide or salt thereof comprising reacting 2,2-diphenyl-2-[(3S)- pyrrolidin-3-yl]acetamide or a salt thereof of claim 24 with a compound of the formula: <img class="EMIRef" id="482902-imgf000025-0001" /> wherein X is a leaving group selected from the group consisting of fluorine, chlorine, bromine, iodine, mesylate, tosylate, nosylate, and brosylate. 29. The process of claim 28, wherein the 2,2-diphenyl-2-[(35)-pyrrolidin-3- yljacetamide or salt thereof has less than about 0.1% by percentage area HPLC 2,2-diphenyl- 2-[(37?)-pyrrolidin-3-yl]acetamide. 30. The process of claim 29, wherein the 2,2-diphenyl-2-[(35)-pyrrolidin-3- yl]acetamide or salt thereof has less than about 0.01% by percentage area HPLC 2,2- diphenyl-2-[(3Λ)-pyrrolidin-3-yl]acetamide.
