2-Pyrrolidinecarboxamide,1-(2-chloroacetyl)-, (2S)- supplier

Name
(S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxaMide
EINECS 1308068-626-2
CAS No. 214398-99-9
Article Data39
CAS DataBase
Density 1.353±0.06 g/cm3(Predicted)
Solubility
Melting Point 133-137℃ (isopropyl ether )
Formula C₇H₁₁ClN₂O₂
Boiling Point 442.5±45.0 °C(Predicted)
Molecular Weight 190.63
Flash Point
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-Pyrrolidinecarboxamide,1-(chloroacetyl)-, (2S)- (9CI);
PSA 63.40000
LogP 0.33970

Synthetic route

: 23500-10-9
(S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid

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

Conditions

Conditions	Yield
With pyridine; di-tert-butyl dicarbonate; ammonium bicarbonate In acetonitrile at 20℃; for 1.5h; Inert atmosphere;	84%
With pyridine; di-tert-butyl dicarbonate; ammonium bicarbonate In acetonitrile at 25℃; for 1.5h;	84%
Stage #1: (S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Cooling with ice; Stage #2: With ammonium carbamate In dichloromethane at 20℃; for 6h;	71.2%

: 79-04-9
chloroacetyl chloride

: 7531-52-4
L-prolinamide

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

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 5℃; for 2h; Reagent/catalyst; Inert atmosphere;	96%
With triethylamine In dichloromethane at -5 - 0℃; for 0.5h; Inert atmosphere;	96.3%
In tetrahydrofuran at 0℃; Reflux; Large scale;	92%

: C7H9Cl2NO2

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

Conditions

Conditions	Yield
With ammonia In dichloromethane for 2h;

: 147-85-3
L-proline

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: chloro-trimethyl-silane / acetonitrile / 1 h / 50 °C 1.2: 20 °C 2.1: thionyl chloride / dichloromethane / 1.17 h / 0 - 20 °C 2.2: 2 h View Scheme
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 2.5 h / 65 - 70 °C 2.1: dicyclohexyl-carbodiimide / dichloromethane / 1 h / 0 - 30 °C 2.2: 3 h / 25 - 30 °C View Scheme
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 3 h / Reflux 2.1: dicyclohexyl-carbodiimide / dichloromethane / 5 h / 20 °C / Cooling with ice 2.2: 6 h / 20 °C View Scheme

: 2577-48-2
methyl (2S)-pyrrolidine carboxylate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonium hydroxide 2: tetrahydrofuran View Scheme
Multi-step reaction with 2 steps 1: ammonium hydroxide / butan-1-ol / 5 - 30 °C 2: N,N-dimethyl-formamide / -5 - 25 °C / Inert atmosphere View Scheme

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

: 565452-98-4
(S)-1-(2-chloroacetyl)-2-cyanopyrrolidine

Conditions

Conditions	Yield
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at 0℃; Large scale;	90%

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

: 96166-39-1
1-glycoloyl-L-proline amide

Conditions

Conditions	Yield
With sodium carbonate In acetone at 50℃; for 5h; Temperature;	93%

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

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

Conditions

Conditions	Yield
With palladium(II) trifluoroacetate; dichloroacetonitrile; water In acetonitrile at 60℃; for 2h; Catalytic behavior; Temperature; Reagent/catalyst; Solvent; Concentration; Schlenk technique; Inert atmosphere;	95%
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at 35 - 48℃; for 4h;	90%
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at 40℃; for 4h;	90%

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

: 1262802-99-2
(S)-1-(2-chloroacetyl)pyrrolidin-2-carboxamide hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol at 70℃;

: 8-(5-nitropyridin-2-yl)-8-azabicyclo[3.2.1]oct-3-yl-exo-amine

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

: (2S)-1-(2-{[8-(5-nitropyridin-2-yl)-8-azabicyclo[3.2.1]oct-3-yl]exo-amino}acetyl)pyrrolidine-2-carbonitrile

Conditions

Conditions	Yield
With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine In acetonitrile	41%

: 3-hydroxy-1-adamantamine

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

: C17H27N3O3

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In tetrahydrofuran at 35℃; for 4h; Temperature; Reflux;

: 121-44-8
triethylamine

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

: {2-[(2S)-2-carbamoylpyrrolidin-1-yl]-2-oxoethyl}triethylazanium chloride

Conditions

Conditions	Yield
In dichloromethane Reflux;	89%

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

: (2S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile

Conditions

Conditions	Yield
With trichlorophosphate at -5 - 20℃;

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

: 202460-48-8
6-[(2-aminoethyl)amino]pyridine-3-carbonitrile

: (S)-1-{2-[2-(5-Cyano-pyridin-2-ylamino)-ethylamino]-acetyl}-pyrrolidine-2-carboxylic acid amide

Conditions

Conditions	Yield
With potassium carbonate In dichloromethane at 0 - 20℃; for 20h;	34%

: 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

: 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%

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

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

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

Conditions

Conditions	Yield
With potassium carbonate In dichloromethane at 0 - 20℃; for 20h;

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

: 247016-69-9
(S)-1-{2-[(5-cyanopyridin-2-yl)amino]ethyl-aminoacetyl}-2-cyano-pyrrolidine

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: 7.82 g / trifluoroacetic anhydride / CH2Cl2 / 1 h / 20 °C 2: 34 percent / tetrahydrofuran / 2 h / cooling View Scheme

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

: 914070-99-8
(S)-1-(2-aminoacetyl)pyrrolidine-2-carbonitrile

Conditions

Conditions	Yield
Stage #1: (S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide With trifluoroacetic anhydride In tetrahydrofuran at 0 - 20℃; for 6h; Stage #2: With ammonium hydroxide at -20 - 20℃; for 3h;

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

: 1-{[(2-phenylethyl)amino]acetyl}-2-pyrrolidinecarbonitrile

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

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

: 1-[2-[(5-nitropyridin-2-yl)amino]ethylamino]acetyl-2-cyano-(S)pyrrolidine

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

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

: (S)-1-(2-Ethylamino-acetyl)-pyrrolidine-2-carbonitrile

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

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

: (S)-1-(2-Isopropylamino-acetyl)-pyrrolidine-2-carbonitrile

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

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

: (S)-1-(2-tert-Butylamino-acetyl)-pyrrolidine-2-carbonitrile

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

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

: (S)-1-(2-Propylamino-acetyl)-pyrrolidine-2-carbonitrile

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

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

: (S)-1-(2-Cyclopropylamino-acetyl)-pyrrolidine-2-carbonitrile

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

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

: (S)-1-(2-Cyclobutylamino-acetyl)-pyrrolidine-2-carbonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 7.82 g / trifluoroacetic anhydride / tetrahydrofuran / 1 h / 20 °C 2: K2CO3 / tetrahydrofuran / 2 h / 0 - 20 °C View Scheme

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

: (S)-1-[2-(1-Ethyl-propylamino)-acetyl]-pyrrolidine-2-carbonitrile

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

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

: (S)-1-[2-(1,1-Dimethyl-propylamino)-acetyl]-pyrrolidine-2-carbonitrile

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

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

: (S)-1-(2-Butylamino-acetyl)-pyrrolidine-2-carbonitrile

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

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

: (S)-1-[2-(1-Isopropyl-2-methyl-propylamino)-acetyl]-pyrrolidine-2-carbonitrile

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

2-Pyrrolidinecarboxamide,1-(2-chloroacetyl)-, (2S)- Chemical Properties

Product Name: 2-Pyrrolidinecarboxamide,1-(2-chloroacetyl)-, (2S)- (CAS NO.214398-99-9)
Molecular Formula: C₇H₁₁ClN₂O₂
Mol File: 214398-99-9.mol

Product Name

(S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxaMide

Synthetic route

2-Pyrrolidinecarboxamide,1-(2-chloroacetyl)-, (2S)- Chemical Properties

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