(2S)-N,N-dimethylpyrrolidine-2-carboxamide

Base Information

• Chemical Name: (2S)-N,N-dimethylpyrrolidine-2-carboxamide
• CAS No.: 29802-22-0
• Molecular Formula: C7H14N2O
• Molecular Weight: 142.201
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50428593
• Nikkaji Number: J1.846.555H
• Wikidata: Q72471971
• Mol file: 29802-22-0.mol

Synonyms:H-Pro-NMe2;29802-22-0;(2S)-N,N-dimethylpyrrolidine-2-carboxamide;(S)-N,N-Dimethylpyrrolidine-2-carboxamide;N,N-Dimethyl-L-prolinamide;L-Proline dimethylamide;(S)-2-(N,N-dimethylcarbamoyl)pyrrolidine;h-pro-nme2, AldrichCPR;L-PRO-NME2;SCHEMBL894617;DTXSID50428593;MLLMAIJXIZOSFS-LURJTMIESA-N;MFCD00083684;AKOS016842962;AC-8665;GS-5428;(s)-2-dimethylaminocarbonyl-pyrrolidine;(S)-2(N,N-dimethylcarbamoyl)pyrrolidine;(S)-N,N-dimethyl-2-pyrrolidinecarboxamide;(S)-2-(N, N-dimethylcarbamoyl)pyrrolidine;CS-0054687;((2S)pyrrolidin-2-yl)-N,N-dimethylcarboxamide;EN300-315122

Chemical Property of (2S)-N,N-dimethylpyrrolidine-2-carboxamide

Chemical Property:

• Vapor Pressure: 0.0219mmHg at 25°C
• Refractive Index: 1.475
• Boiling Point: 250.2 °C at 760 mmHg
• PKA: 9.18±0.10(Predicted)
• Flash Point: 105.1 °C
• PSA: 32.34000
• Density: 1.017 g/cm³
• LogP: 0.15540
• Storage Temp.: -15°C
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 142.110613074
• Heavy Atom Count: 10
• Complexity: 134

Purity/Quality:

99% ^*data from raw suppliers

L-Proline dimethylamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C(=O)C1CCCN1
• Isomeric SMILES: CN(C)C(=O)[C@@H]1CCCN1
• Uses: L-Proline Dimethylamide is a reactant used in the synthesis of fluoromethylsulfonylaminophenyl propanamides as TRPV1 antagonists.

Technology Process of (2S)-N,N-dimethylpyrrolidine-2-carboxamide

There total 9 articles about (2S)-N,N-dimethylpyrrolidine-2-carboxamide 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: 76.0%

(2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one (118916-60-2,97538-67-5) + dimethyl amine (124-40-3) → (S)-pyrrolidin-2-carboxylic acid dimethylamide (29802-22-0,433980-61-1)

Guidance literature:

In ethanol; at 20 ℃; for 0.166667h;

DOI:10.1016/S0957-4166(02)00579-7

Reference yield:

(S)-2-Dimethylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester (42718-55-8) → (S)-pyrrolidin-2-carboxylic acid dimethylamide (29802-22-0,433980-61-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1016/S0960-894X(03)00533-X

Reference yield:

N-Benzyloxycarbonyl-L-proline (1148-11-4) → (S)-pyrrolidin-2-carboxylic acid dimethylamide (29802-22-0,433980-61-1)

Guidance literature:

Multi-step reaction with 2 steps

1: EDC; HOAt / dimethylformamide

2: H₂ / Pd/C / methanol

With 1-hydroxy-7-aza-benzotriazole; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00533-X

upstream raw materials:

(2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one

dimethyl amine

(S)-2-Dimethylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

N-Benzyloxycarbonyl-L-proline

Downstream raw materials:

N-acetyl-(2S)-proline dimethyl amide

N-thioacetyl-(2S)-proline dimethyl amide

Refernces

• 1、 Mandal, Pijus K.,Morlacchi, Pietro,Knight, J. Morgan,Link, Todd M.,Lee, Gilbert R.,Nurieva, Roza,Singh, Divyendu,Dhanik, Ankur,Kavraki, Lydia,Corry, David B.,Ladbury, John E.,McMurray, John S.. "Targeting the Src Homology 2 (SH2) Domain of Signal Transducer and Activator of Transcription 6 (STAT6) with Cell-Permeable, Phosphatase-Stable Phosphopeptide Mimics Potently Inhibits Tyr641 Phosphorylation and Transcriptional Activity". . p. 8970 - 8984. Retrieved 2015/12/09.
• 2、 Diakos, Connie I.,Zhang, Mei,Beale, Philip J.,Fenton, Ronald R.,Hambley, Trevor W.. "Synthesis, characterisation and in vitro cytotoxicity studies of a series of chiral platinum(II) complexes based on the 2-aminomethylpyrrolidine ligand: X-ray crystal structure of [PtCl2(R-dimepyrr)] (R-dimepyrr = N-dimethyl-2(R)-aminomethylpyrrolidine)". experimental part. p. 2807 - 2814. Retrieved 2009/10/10.