(2R)-pyrrolidin-1-ium-2-carboxylate

Base Information

• Chemical Name: (2R)-pyrrolidin-1-ium-2-carboxylate
• CAS No.: 344-25-2
• Molecular Formula: C5H9NO2
• Molecular Weight: 225.168
• Hs Code.: 2922.49
• Mol file: 344-25-2.mol

Synonyms:(2R)-pyrrolidin-1-ium-2-carboxylate;D-proline zwitterion;CHEBI:57726;(2R)-pyrrolidinium-2-carboxylate

Chemical Property of (2R)-pyrrolidin-1-ium-2-carboxylate

Chemical Property:

• Appearance/Colour: White to off-white powder
• Melting Point: 223 °C (dec.)(lit.)
• Refractive Index: 85 ° (C=4, H2O)
• Boiling Point: 252.2 °C at 760 mmHg
• PKA: 1.952(at 25℃)
• Flash Point: 106.3 °C
• PSA: 49.33000
• Density: 1.186 g/cm³
• LogP: 0.15180
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Solubility.: Methanol (Slightly), Water (Sparingly)
• Water Solubility.: soluble >1000 g/L (20 ºC)
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 115.063328530
• Heavy Atom Count: 8
• Complexity: 97.1

Purity/Quality:

98.0% ^*data from raw suppliers

D-Proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-36/37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC([NH2+]C1)C(=O)[O-]
• Isomeric SMILES: C1C[C@@H]([NH2+]C1)C(=O)[O-]
• Uses: Used in the synthesis of (R)-(+)-N-Boc-Pipecolic Acid, (S)-(-)-Coniine, (S)-(+)-Pelletierine, (+)-.beta.-Conhydrine, and (S)-(-)-Ropivacaine and formal synthesis of (-)-Lasubine II and (+)-Cermizine C. Labelled D-Proline Lasubine II and (+)-Cermizine C. proline is a skin-conditioning agent. An amino acid found in the collagen molecule.

Technology Process of (2R)-pyrrolidin-1-ium-2-carboxylate

There total 54 articles about (2R)-pyrrolidin-1-ium-2-carboxylate 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: 96.0%

Z-D-proline (6404-31-5) → D-Prolin (344-25-2,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 5h; under 760 Torr;

DOI:10.1039/a704915c

Reference yield: 95.65%

(S)-1-Pyrrolidin-2-yl-methanol (23356-96-9) → D-Prolin (344-25-2,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

With potassium permanganate; In water; at 15 - 20 ℃; Concentration;

Reference yield: 83.0%

(R)-1-(benzyloxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid → D-Prolin (344-25-2,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

With hydrogen; palladium(II) hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 3h;

DOI:10.1055/s-0034-1378452

upstream raw materials:

(R)-N-(3,5-dinitrobenzoyl)proline

(2R,5R)-2-t-butyl-1-t-butyloxycarbonyl-5-(3-chloropropyl)-3-methyl-4-imidazolidinone

(2S,3S)-2,3-Dihydroxy-succinic acid; compound with (R)-pyrrolidine-2-carboxylic acid

(S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide

Downstream raw materials:

5-amino-2-oxo-valeric acid

D-proline methyl ester hydrochloride

ethyl proline hydrochloride

Z-D-proline

Refernces

Facile synthesis of benzo-fused 2,8-dioxabicyclo[3.3.1]nonane derivatives via a domino Knoevenagel condensation/hetero-Diels-Alder reaction sequence

10.1016/j.tet.2007.11.036

The study presents a two-step synthesis method for benzo-fused 2,8-dioxabicyclo[3.3.1]nonane derivatives, utilizing a domino Knoevenagel condensation/intramolecular hetero-Diels-Alder reaction sequence. The process involves an initial intermolecular Knoevenagel condensation of a compound with active methylene compounds to form a heterodiene, which then undergoes intramolecular hetero-Diels-Alder cycloaddition. The research successfully optimized the reaction conditions, including the choice of catalyst and solvent, to achieve high yields of the desired products. The method demonstrates a novel route for constructing complex heterocycles with potential applications in medicinal chemistry.

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