(2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile

Base Information

• Chemical Name: (2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile
• CAS No.: 207557-35-5
• Molecular Formula: C7H9ClN2O
• Molecular Weight: 172.614
• Hs Code.: 2942000000
• European Community (EC) Number: 807-388-8
• DSSTox Substance ID: DTXSID00454201
• Nikkaji Number: J1.722.426C
• Wikidata: Q72516913
• Mol file: 207557-35-5.mol

Synonyms:207557-35-5;(2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile;(S)-1-(2-Chloroacetyl)pyrrolidine-2-carbonitrile;(2S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile;(S)-1-(2-Chloroacetyl)-pyrrolidine-2-carbonitrile;(S)-1-(2-Chloro-acetyl)-pyrrolidine-2-carbonitrile;2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)-, (2S)-;2-Pyrrolidinecarbonitrile, 1-(2-chloroacetyl)-, (2S)-;(2S)-1-(chloroacetyl)pyrrolidine-2-carbonitrile;(2S)-1-(2-Chloroacetyl)-2-9-pyrrolidinecarbonitrile;MFCD08689902;SCHEMBL605418;DTXSID00454201;YCWRPKBYQZOLCD-LURJTMIESA-N;(2S)-1-(2-Chloroacetyl)-2-pyrrolidinecarbonitrile;(2S)-1-chloroacetylpyrrolidine-2-carbonitrile;CS-D1786;AKOS006291018;AKOS016015838;AC-8547;(2S)-N-chloroacetyl-2-cyanopyrrolidine;DS-13426;AM20090696;C3202;1-(Chloroacetyl)pyrrolidine-2alpha-carbonitrile;(S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile;EN300-1698838;1-(2-Chloroacetyl)pyrrolidine-2-(S)-carbonitrile;A814859;(S)-1-(2'-Chloroacetyl)pyrrolidine-2-carbonitrile;(S)-1-(2-Chloro-acetyl)pyrrolidine-2-carbonitrile;Q-200012;Z1198180839;1-(2-chloroacetyl)pyrrolidine-2-carbonitrile

Chemical Property of (2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 52-53 °C
• Refractive Index: 1.519
• Boiling Point: 363.149 °C at 760 mmHg
• PKA: -4.65±0.40(Predicted)
• Flash Point: 173.427 °C
• PSA: 44.10000
• Density: 1.273 g/cm³
• LogP: 0.67768
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 172.0403406
• Heavy Atom Count: 11
• Complexity: 208

Purity/Quality:

99% up, ^*data from raw suppliers

(2S)-1-(2-Chloroacetyl)-2-9-pyrrolidinecarbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)CCl)C#N
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)CCl)C#N
• Uses: (2S)-1-(2-Chloroacetyl)-2-9-pyrrolidinecarbonitrile is a key intermediate for dipeptidyl peptidase IV inhibitor Vildagliptin (V305000).

Technology Process of (2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile

There total 26 articles about (2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide (214398-99-9) → (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile (207557-35-5)

Guidance literature:

With palladium(II) trifluoroacetate; dichloroacetonitrile; water; In acetonitrile; at 60 ℃; for 2h; Temperature; Reagent/catalyst; Solvent; Concentration; Catalytic behavior; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.9b01657

Reference yield: 93.0%

(2S)-pyrrolidine-2-carbonitrile (204387-53-1) + chloroacetyl chloride (79-04-9) → (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile (207557-35-5)

Guidance literature:

With triethylamine; In dichloromethane; for 2h; Reflux;

Reference yield: 93.0%

1-glycoloyl-L-proline amide (96166-39-1) → (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile (207557-35-5)

Guidance literature:

With trichlorophosphate; In N,N-dimethyl-formamide; at 0 ℃; for 3h; Heating;

upstream raw materials:

(S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide

L-prolinamide

L-proline

L-proline

Downstream raw materials:

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

Refernces

• 1、 Kushwaha, Ram N.,Srivastava, Rohit,Mishra, Akansha,Rawat, Arun K.,Srivastava, Arvind K.,Haq, Wahajul,Katti, Seturam B.. "Design, synthesis, biological screening, and molecular docking studies of piperazine-derived constrained inhibitors of DPP-IV for the treatment of type 2 diabetes". . p. 439 - 446. Retrieved 2015.
• 2、 -. "Production method of vildagliptin". Paragraph 0079-0081; 0085-0087; 0096-0103. . Retrieved 2021/10/27.
• 3、 Zhang, Li,Jiang, Lan,Guan, Xiaoshu,Cai, Linhong,Wang, Jingyu,Xiang, Peng,Pan, Junyi,Hu, Xiangnan. "A facile method to synthesize vildagliptin". . p. 305 - 309. Retrieved 2020/12/01.