Substituted quinolinylcyclohexylpropanamide compounds and improved methods for their preparation

A method of making a compound of formula I, or a stereoisomer thereof:

• comprising
• contacting a compound of formula II, or a stereoisomer thereof:
• wherein R1 is C1-6alkyl, aryl, or C1-6haloalkyl;
• with a mixture of a C1-6alkoxide salt and a di-C1-6alkyl-malonate, in a suitable organic solvent;
• for a time and at a temperature sufficient to displace the sulfonate moiety and to produce a compound of formula III, or a stereoisomer thereof:
• and
• contacting the compound of formula III, or a stereoisomer thereof, with a suitable organic acid, in a suitable aqueous organic solvent, for a time and at a temperature sufficient for hydrolysis and decarboxylation and to produce the compound of formula I, or a stereoisomer thereof.