Process for production of glycopyrronium tosylate

1. A glycopyrrolate base composition comprising threo-glycopyrrolate base and erythro-glycopyrrolate base, wherein the threo-glycopyrrolate base is at least 95% of the total glycopyrrolate base content of the composition and the erythro-glycopyrrolate base is less than 5% of the total glycopyrrolate base content of the composition.

2. The glycopyrrolate base composition of claim 1 , wherein the threo-glycopyrrolate base is at least 96% of the total glycopyrrolate base content of the composition and the erythro-glycopyrrolate base is less than 4% of the total glycopyrrolate base content of the composition.

3. The glycopyrrolate base composition of claim 1 , wherein the threo-glycopyrrolate base is at least 97% of the total glycopyrrolate base content of the composition and the erythro-glycopyrrolate base is less than 3% of the total glycopyrrolate base content of the composition.

4. A glycopyrrolate base composition comprising threo-glycopyrrolate base and erythro-glycopyrrolate base, wherein the composition is produced by:

(i) contacting cyclopentylmandelic acid with 1-methylpyrrolidin-3-ol to form glycopyrrolate base:

(ii) contacting the glycopyrrolate base with 5-nitroisophthalic acid to form glycopyrrolate base, 5-nitroisophthalate salt:

and

(iii) contacting the glycopyrrolate base, 5-nitroisophthalate salt with an inorganic base to form glycopyrrolate base:

(iv) purifying the glycopyrrolate base obtained in step (iii) by contacting it with an organic solvent to obtain a purified glycopyrrolate base; wherein the organic solvent is a water-immiscible organic solvent.

5. A method of producing a glycopyrrolate tosylate composition comprising threo-glycopyrronium tosylate and erythro-glycopyrronium tosylate, wherein:

the threo-glycopyrronium tosylate is at least 95% of the total glycopyrrolate tosylate content of the composition;

the erythro-glycopyrronium tosylate is less than 5% of the total glycopyrrolate base content of the composition; and

the composition is produced by glycopyrronium base:

contacting the glycopyrronium base composition of claim 1 with methyl tosylate to produce glycopyrronium tosylate:

6. The method of claim 5 , wherein the threo-glycopyrronium tosylate is at least 96% of the total glycopyrronium tosylate content of the composition and the erythro-glycopyrronium tosylate is less than 4% of the total glycopyrronium tosylate content of the composition.

7. The method of claim 5 , wherein the threo-glycopyrronium tosylate is at least 97% of the total glycopyrronium tosylate content of the composition and the erythro-glycopyrronium tosylate is less than 3% of the total glycopyrronium tosylate content of the composition.

8. The method of claim 5 , wherein the threo-glycopyrronium tosylate is at least 99% of the total glycopyrronium tosylate content of the composition and the erythro-glycopyrronium tosylate is less than 1% of the total glycopyrronium tosylate content of the composition.

9. The method of claim 5 , wherein the threo-glycopyrronium tosylate is at least 99.5% of the total glycopyrronium tosylate content of the composition and the erythro-glycopyrronium tosylate is less than 0.5% of the total glycopyrronium tosylate content of the composition.

10. The method of claim 5 , wherein the threo-glycopyrronium tosylate is at least 99.6% of the total glycopyrronium tosylate content of the composition and the erythro-glycopyrronium tosylate is less than 0.4% of the total glycopyrronium tosylate content of the composition.

11. The composition of claim 4 , wherein the organic solvent is selected from a group consisting of: benzene, n-butanol, carbon tetrachloride, chloroform, cyclohexane, ethylene chloride, heptane, hexane, pentane, toluene, trichloroethylene, and xylene.

12. The composition of claim 11 , wherein the organic solvent is toluene.