Novel salt of dimethyl-2,3-dihydro-1h-indene derivative and processes for preparing the same

A process for preparing a (1S)-(+)-10-camphorsulfonic acid salt of (S)-quinuclidin-3-yl ((R)-5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate, the process of which comprises:

• (a) dissolving (S)-quinuclidin-3-yl ((R)-5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate and (1S)-(+)-10-camphorsulfonic acid in a solvent under heating to obtain a solution;
• and
• (b) cooling the solution obtained in the step (a) to form a precipitate.

A process for preparing a (1S)-(+)-10-camphorsulfonic acid salt of (S)-quinuclidin-3-yl ((R)-5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate, the process of which comprises:

• (i) dissolving (S)-quinuclidin-3-yl ((R)-5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate and (1S)-(+)-10-camphorsulfonic acid in a solvent at 5° C. to 30° C. to obtain a solution;
• and
• (ii) adding an anti-solvent to the solution obtained in the step (i) to form a precipitate.

A process for preparing a (1S)-(+)-10-camphorsulfonic acid salt of (S)-quinuclidin-3-yl ((R)-5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate, the process of which comprises:

• (p) dissolving (S)-quinuclidin-3-yl ((R)-5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-in den-1-yl)carbamate and (1S)-(+)-10-camphorsulfonic acid in a solvent at 5° C. to 30° C. to obtain a solution;
• and
• (q) evaporating the solvent from the solution obtained in the step (p).