Name: Saxagliptin hydrochloride
SKU: 709031-78-7

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Basic Information

Synthetic route

Conditions	Yield
With hydrogenchloride In water; ethyl acetate at 5 - 10℃;	99%
With chloro-trimethyl-silane In acetone for 1h;
Multi-step reaction with 2 steps 1: 20 - 30 °C 2: hydrogenchloride; water / acetone / 1.25 h View Scheme

: (1S,3S,5S)-2-[(2S)-2-tritylamino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Conditions	Yield
With hydrogenchloride; water In methanol at 25℃; for 3h;	90%

Conditions	Yield
Stage #1: C25H31N3O2 With palladium 10% on activated carbon In methanol at 25 - 30℃; for 2h; Stage #2: With hydrogenchloride In ethyl acetate at 25 - 30℃; for 4h;	80%
Stage #1: C25H31N3O2 With palladium 10% on activated carbon In methanol at 25 - 30℃; for 2h; Stage #2: With hydrogenchloride In water; ethyl acetate at 25 - 30℃; for 4h;	80%

Conditions	Yield
Stage #1: C18H23N5O2 With ammonium chloride; zinc In methanol; water at 25 - 30℃; for 2h; Stage #2: With hydrogenchloride In water at 25 - 30℃; for 4h;	73%
Stage #1: C18H23N5O2 With ammonium chloride; zinc In methanol; water at 25 - 30℃; for 2h; Stage #2: With hydrogenchloride In water; ethyl acetate at 25 - 30℃; for 4h;	73%

Conditions	Yield
In ethanol at 45℃;

: 709031-43-6
3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / isopropyl alcohol; water / 2.08 h / 20 - 65 °C 2: 20 - 30 °C 3: hydrogenchloride; water / acetone / 1.25 h View Scheme
With hydrogenchloride In propan-1-ol; water Product distribution / selectivity; Reflux;
With hydrogenchloride; water In isopropyl alcohol at 20 - 65℃; for 1h;	50 g
With dichloromethane In methanol at 20℃; Inert atmosphere;

: 361442-01-5
tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 0.5 h / 0 °C 1.2: 0.58 h / 0 - 7 °C 2.1: hydrogenchloride / isopropyl alcohol; water / 2.08 h / 20 - 65 °C 3.1: 20 - 30 °C 4.1: hydrogenchloride; water / acetone / 1.25 h View Scheme
Multi-step reaction with 2 steps 1: triethylamine; trifluoroacetyl chloride / dichloromethane / 0 - 10 °C 2: hydrogenchloride / water; propan-1-ol / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: pyridine; trifluoroacetic anhydride / 0.5 h / Cooling with ice 1.2: 7.55 h / Cooling 2.1: dichloromethane / methanol / 20 °C / Inert atmosphere View Scheme

: 1346445-79-1
(1S,3S,5S)-2-[(2S)-2-propan-2-ylideneamino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]-hexane-3-carbonitrile

Conditions	Yield
With hydrogenchloride; water In acetone for 1.25h;
With ammonium chloride at 20℃; pH=4.53;

: 361442-05-9
(S)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt

Conditions	Yield
Stage #1: (S)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt With sodium hydroxide In water Stage #2: With hydrogenchloride In dichloromethane; water

: benzyl N-[(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hexan-2-yl]-1-(3-hydroxyadamantan-1-yl)-2-oxoethyl]carbamate

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trifluoroacetic anhydride; 3-pyridinecarboxylic acid ethyl ester / ethyl acetate / 6 h / 0 - 5 °C 1.2: 2 h / 25 °C 2.1: 5%-palladium/activated carbon; hydrogen / acetonitrile / 4 h / 20 - 25 °C 3.1: hydrogenchloride / water; ethyl acetate / 5 - 10 °C View Scheme