Pyrrolidine-3-carboxylic acid

Base Information

• Chemical Name: Pyrrolidine-3-carboxylic acid
• CAS No.: 59378-87-9
• Molecular Formula: C5H9NO2
• Molecular Weight: 115.13
• Hs Code.: 2933990090
• European Community (EC) Number: 696-313-0
• UNII: XQ9918NB1D
• DSSTox Substance ID: DTXSID20900992
• Nikkaji Number: J457.359E
• Wikidata: Q27293960
• ChEMBL ID: CHEMBL4586784
• Mol file: 59378-87-9.mol

Synonyms:P-3-carboxylic acid;pyrrolidine-3-carboxylic acid;S-pyrrolidine-3-carboxylic acid

Chemical Property of Pyrrolidine-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 0.00615mmHg at 25°C
• Melting Point: 183-185 °C(Solv: methanol (67-56-1); acetone (67-64-1))
• Refractive Index: 1.487
• Boiling Point: 252.2 °C at 760 mmHg
• PKA: 3.86±0.20(Predicted)
• Flash Point: 106.3 °C
• PSA: 86.63000
• Density: 1.186 g/cm³
• LogP: 0.64260
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Methanol (Sparingly, Sonicated), Water (Slightly)
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 115.063328530
• Heavy Atom Count: 8
• Complexity: 103

Purity/Quality:

98%,99%, ^*data from raw suppliers

Pyrrolidine-3-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36

MSDS Files:

Useful:

• Canonical SMILES: C1CNCC1C(=O)O

Technology Process of Pyrrolidine-3-carboxylic acid

There total 10 articles about Pyrrolidine-3-carboxylic acid 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: 1.8%

pyrrolidine (123-75-1) + formic acid (64-18-6) → pyrrolidine-3-carboxylic acid (59378-87-9,68464-02-8,72580-53-1,72580-54-2) + glycine (56-40-6,18875-39-3,25718-94-9) + rac-Pro-OH (609-36-9,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

In water; at 10 - 20 ℃; for 1h; contact glow discharge electrolysis (500-600 V, 45 mA);

Reference yield: 0.4%

pyrrolidine (123-75-1) + sodium formate (141-53-7) → pyrrolidine-3-carboxylic acid (59378-87-9,68464-02-8,72580-53-1,72580-54-2) + glycine (56-40-6,18875-39-3,25718-94-9) + rac-Pro-OH (609-36-9,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

In water; at 10 - 20 ℃; for 1h; contact glow discharge electrolysis (500-600 V, 45 mA);

Reference yield:

C10H17NO3 (191348-04-6) → pyrrolidine-3-carboxylic acid (59378-87-9,68464-02-8,72580-53-1,72580-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium dichromate / N,N-dimethyl-formamide; toluene / 20 °C

2: hydrogenchloride / water

With hydrogenchloride; pyridinium dichromate; In water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja210117z

upstream raw materials:

pyrrolidine-1,3-dicarboxylic acid diethyl ester

pyrrolidine

formic acid

sodium formate

Downstream raw materials:

3-(4-chloro-benzylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

1-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-4-fluoro-1H-indazol-3-yl)pyrrolidine-3-carboxylic acid

Refernces

• 1、 Chikkali, Samir H.,Bellini, Rosalba,De Bruin, Bas,Van Der Vlugt, Jarl Ivar,Reek, Joost N. H.. "Highly selective asymmetric Rh-catalyzed hydroformylation of heterocyclic olefins". . p. 6607 - 6616. Retrieved 2012/06/15.