Processes for the preparation of SGLT2 inhibitors

A method for the preparation of a complex of Formula IA:

• wherein the subscript n is 1 or 2;
• R1 is a member selected from the group consisting of hydrogen, halo and C1-C6 alkyl;
• V is a member selected from the group consisting of oxygen and a single bond;
• W is a member selected from the group consisting of C1-C6 alkylene, C2-C6 alkenylene, C2-C6 alkynylene, C3-C10 cycloalkylene, and (C3-C10 cycloalkylene)(C1-C6 alkylene) wherein the C3-C10 cycloalkylene portion bonds to V and the C1-C6 alkylene portion bonds to X;
• X is a member selected from the group consisting of oxygen and NRa;
• Y is a member selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C6 hydroxyalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C10 cycloalkyl, (C3-C10 cycloalkyl)C1-C4 alkyl, (C1-C4 alkyloxy)C1-C3 alkyl, (C3-C10 cycloalkyloxy)C1-C3 alkyl, (amino)C1-C3 alkyl, (C1-C4 alkylamino)C1-C3 alkyl, (C1-C6 alkyl)carbonyl, (C2-C6 alkenyl)carbonyl, (C2-C6 alkynyl)carbonyl, (C1-C6 alkyl)sulfonyl, (C2-C6 alkenyl)sulfonyl, and (C2-C6 alkynyl)sulfonyl,
• wherein alkyl, alkenyl, alkynyl, cycloalkyl and cycloalkenyl groups or portions of W, X and Y are optionally partly or completely fluorinated and are optionally mono- or disubstituted by substituents independently selected from the group consisting of chlorine, hydroxy, C1-C3 alkyl, C1-C3 alkoxy, and C3-C6 cycloalkyl, and in cycloalkyl groups or portions one or two methylene groups are optionally replaced independently of one another by O, S, CO, SO, SO2 or NRb, and one or two methyne groups are optionally replaced by N, wherein the heterocycle formed by said optional replacement is other than heteroaryl;
• and
• Ra is a member independently selected from the group consisting of H, C1-C6 alkyl, C3-C6 cycloalkyl and (C1-C4 alkyl)carbonyl, wherein alkyl and cycloalkyl groups or portions are optionally partly or completely fluorinated;
• each Rb is a member independently selected from the group consisting of H, C1-C4 alkyl and (C1-C4 alkyl)carbonyl, wherein alkyl groups or portions are optionally partly or completely fluorinated;
• and pharmaceutically acceptable salts thereof;
• comprising:
• (a) reacting a compound of Formula II
• with a reducing agent in the presence of an activating group to form a compound of Formula III
• and
• (b) contacting said compound of Formula III with an amino acid to form said complex of Formula IA;
• wherein steps (a) and (b) are performed without purification of said compound of Formula III and wherein steps (a) and (b) are performed sequentially without an intervening protection or deprotection step.