Name: Vildagliptin
SKU: 274901-16-5

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Basic Information

Molecular Structure:
CAS No.:	274901-16-5
Name:	Vildagliptin

Formula:	C₁₇H₂₅N₃O₂
Molecular Weight:	303.404
Synonyms:	2-Pyrrolidinecarbonitrile,1-[[(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)amino]acetyl]-, (2S)- (9CI);Galvus;LAF 237;NVP-LAF 237;(-)-(2s)-1-(((3-hydroxytricyclo(3.3.1.1(3,7))dec-1-yl)amino)acetyl)pyrrolidine-2-carbonitrile;
EINECS:	630-410-0
Density:	1.27 g/cm³
Melting Point:	153-155?C
Boiling Point:	531.3 °C at 760 mmHg
Flash Point:	275.1 °C
Appearance:	white crystalline powder
Risk Codes:	28-38-41-48
Safety:	24/25-26-28-36/37/39
PSA:	76.36000
LogP:	1.50308

Synthetic route

: 1-[2-(3-hydroxyadamant-1-yl-amino)acetyl]pyrrolidin-(2S)-carbonitrile calcium(II)-chloride

: 274901-16-5
vildagliptin

Conditions

Conditions	Yield
With sodium carbonate; sodium chloride In dichloromethane at 20 - 40℃; Product distribution / selectivity;	95%
With sodium carbonate In water at 40℃; for 0.0333333h; Product distribution / selectivity;	75%

: (2S)‐1‐[[(3-hydroxytricyclo[3.3.1.1[3,7]]decane-1-yl)imino]acetyl]pyrrolidine-2-carbonitrile

: 274901-16-5
vildagliptin

Conditions

Conditions	Yield
With palladium on activated charcoal; ammonium formate In tetrahydrofuran at 20℃; for 8h; Reagent/catalyst; Solvent; Temperature;	91.9%
With palladium on activated charcoal; ammonium formate In tetrahydrofuran at 20℃; for 10h; Solvent; Reagent/catalyst; Temperature;	91.9%

: 1032564-18-3
(3-hydroxyadamantan-1-ylamino)acetic acid

: (S)-pyrrolidine-2-carbonitrile p-toluenesulfonate

: 274901-16-5
vildagliptin

Conditions

Conditions	Yield
Stage #1: C12H14N2O3S With sodium hydroxide In dichloromethane at 0℃; for 1.5h; Stage #2: (3-hydroxyadamantan-1-ylamino)acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0℃; Concentration;	90.8%

: C16H33NOSi2

: 207557-35-5
(S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile

: 274901-16-5
vildagliptin

Conditions

Conditions	Yield
Stage #1: C16H33NOSi2; (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile With N-ethyl-N,N-diisopropylamine; potassium iodide In acetonitrile at 75 - 80℃; for 3h; Stage #2: With ethanol In acetonitrile for 2h; Reagent/catalyst;	88.3%

: 702-82-9
3-aminoadamantan-1-ol

: 207557-35-5
(S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile

: 274901-16-5
vildagliptin

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In tetrahydrofuran; butanone at 40℃; for 3h;	82%
With potassium carbonate; potassium iodide In tetrahydrofuran; butanone at 40℃; for 3h; Reflux;	82%
With potassium carbonate; potassium iodide In acetone at 50 - 55℃; for 3h; Solvent;	82.2%

: 702-82-9
3-aminoadamantan-1-ol

: (S)-pyrrolidine-2-carbonitrile p-toluenesulfonate

: 79-04-9
chloroacetyl chloride

: 274901-16-5
vildagliptin

Conditions

Conditions	Yield
Stage #1: (S)-pyrrolidine-2-carbonitrile p-toluenesulfonate; chloroacetyl chloride With triethylamine In dichloromethane at 0 - 5℃; for 2h; Stage #2: 3-aminoadamantan-1-ol In water for 4h; Temperature; Reflux;	76.9%

...Expand

: (S)-1-[2-(3-hydroxyadamantan-1-ylamino)acetyl]pyrrolidine-2-carboxylic acid amide

: 274901-16-5
vildagliptin

Conditions

Conditions	Yield
Stage #1: (S)-1-[2-(3-hydroxyadamantan-1-ylamino)acetyl]pyrrolidine-2-carboxylic acid amide With trifluoroacetic acid; trifluoroacetic anhydride In 2-methyltetrahydrofuran Reflux; Stage #2: With potassium carbonate In 2-methyltetrahydrofuran; water at 5 - 10℃; Reagent/catalyst;	75%
With trichlorophosphate In dichloromethane at 10℃; for 4h; Reagent/catalyst; Solvent; Temperature; Time; Reflux;	4.53 g

: 702-82-9
3-aminoadamantan-1-ol

: 214398-99-9
(S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide

: 274901-16-5
vildagliptin

Conditions

Conditions	Yield
Stage #1: (S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide With trifluoroacetic anhydride In tetrahydrofuran at 20℃; for 2h; Cooling with ice; Stage #2: 3-aminoadamantan-1-ol With potassium carbonate; potassium iodide In tetrahydrofuran at 40℃; for 8.5h; Time; Reflux;	71%

: (S)-1-{2-[benzyl(3-hydroxyadamantan-1-yl)amino]acetyl}pyrrolidine-2-carbonitrile

: 274901-16-5
vildagliptin

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃;	61.5%
With palladium 10% on activated carbon; hydrogen In methanol for 22h;

: 214398-99-9
(S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide

: 274901-16-5
vildagliptin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 7.82 g / trifluoroacetic anhydride / tetrahydrofuran / 1 h / 20 °C 2: K2CO3 / tetrahydrofuran / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C 2: potassium carbonate; potassium iodide / tetrahydrofuran / 5 h / 60 - 65 °C View Scheme
Multi-step reaction with 2 steps 1.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 4 h / 35 - 48 °C 2.1: potassium carbonate; potassium iodide / butanone / 40 °C 2.2: 3 h / 38 - 75 °C View Scheme
Multi-step reaction with 2 steps 1.1: trichlorophosphate / -5 - 20 °C 2.1: potassium carbonate; potassium iodide / acetone / 0.25 h / 20 °C 2.2: 40 - 65 °C View Scheme