Benzyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-(3-hydroxyadamantan-1-yl)-2-oxo ethyl]carbamate → Saxagliptin

Participants

Reaction Steps

To a solution of benzyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-(3-hydroxyadamantan-1-yl)-2-oxo-ethyl]carbamate (10 gm) (formula-IX) in methanol 5% Pd/C (50% wet, 1 gm) was added. Hydrogen gas was bubbled through the reaction mass for 2 hrs at 20-25° C. After the starting material was completely converted, the reaction mass was filtered. The filtrate was evaporated to yield SAXAGLIPTIN free base of formula-I as a foamy solid. To the solid ethyl acetate (5 ml), 20 micro liters of water and n-hexane (20 ml) were added, stirred at 0-5° C. and filtered the white solid formed to yield 6.98 gm (94%) of SAXAGLIPTIN MONO HYDRATE. HPLC Purity: 99.5% (A) and the content of the impurity cyclic amidine: 0.09% (A), M.P: 105-108° C.

Provenance & Evidence