Processes for the preparation of (R)-2-(7-4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[B]indol-3-yl)acetic acid and salts thereof

A process for preparing a compound of Formula (IIk):

• wherein R3 is C1-C6 alkyl;
• comprising the step of alkylating a compound of Formula (IIj):
• with 4-(chloromethyl)-1-cyclopentyl-2-(trifluoromethyl)benzene (Formula (IIc)):
• in the presence of an alkylating-step base, and an alkylating-step solvent to form said compound of Formula (IIk),
• provided that said alkylating-step solvent is other than a solvent of the group consisting of dimethylformamide (DMF) and dimethylacetamide (DMA).

A process for preparing a compound of Formula (IIj):

• wherein R3 is C1-C6 alkyl;
• comprising the step of reducing a compound of Formula (IIi):
• wherein R4, R5, and R6 are each selected independently from the group consisting of H, C1-C4 alkyl, C1-C4 alkoxy, halogen, C1-C4 haloalkyl, C1-C4 haloalkoxy, and nitro;
• in the presence of a reducing-step agent, and a reducing-step catalyst, to form said compound of Formula (IIj).

A process for preparing a compound of Formula (IIi):

• wherein R3 is C1-C6 alkyl;
• and R4, R5, and R6 are each selected independently from the group consisting of H, C1-C4 alkyl, C1-C4 alkoxy, halogen, C1-C4 haloalkyl, C1-C4 haloalkoxy, and nitro;
• comprising the step of reacting a compound of Formula (IIg):
• wherein R1 and R2 are each independently C1-C6 alkyl, or R1 and R2 together with the nitrogen atom to which they are both bonded form a 5-member or 6-member heterocyclic ring;
• with a compound of Formula (IIh) or a salt thereof,
• wherein R4, R5, and R6 are each selected independently from the group consisting of H, C1-C4 alkyl, C1-C4 alkoxy, halogen, C1-C4 haloalkyl, C1-C4 haloalkoxy, and nitro;
• in the presence of an indole-forming acid, to form a compound of Formula (IIi).