Patent ID: 8748631

Claim:
A method for making saxagliptin hydrochloride monohydrate comprising: combining (S)-(+)-p-toluenesulfinamide Ti(OEt) 4 and adamantane 1-carboxaldehyde to obtain wherein R is alkyl or aryl, treating the resulting compound with NaCN, KCN, trimethylsilyl cyanide (TMSCN) or Et 2 AlCN and (S)-(+)-p-toluenesulfonamide/Ti(OEt) 4 to obtain treating the resulting compound with phthalic anhydride to obtain treating the resulting compound with acid to obtain treating the resulting compound with KMnO 4 to obtain coupling the resulting compound with methanoproline nitrile using hydroxybenzotriazole (HOBT), 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (EDC HCl) or N,N-diisopropylethylamine (DIPEA) to obtain treating the resulting compound with methyl amine and hydrochloric acid.