73858-59-0

Basic information

• Product Name: 2-Pyrrolidinylphosphonic Acid
• Synonyms: 2-Pyrrolidinylphosphonic Acid;BTURSMUPRYMLJE-UHFFFAOYSA-N
• CAS NO: 73858-59-0
• Molecular Formula: C4H10NO3P
• Molecular Weight: 151.100861
• Mol File: 73858-59-0.mol

Chemical Properties

• Melting Point: 275 °C (decomp)
• Boiling Point: 359.3±52.0 °C(Predicted)
• Appearance: /
• Density: 1.42±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Sparingly, Heated, Sonicated), Water (Slightly)
• PKA: 0.95±0.20(Predicted)
• CAS DataBase Reference: 2-Pyrrolidinylphosphonic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyrrolidinylphosphonic Acid(73858-59-0)
• EPA Substance Registry System: 2-Pyrrolidinylphosphonic Acid(73858-59-0)

Safety Data

• Hazardous Substances Data: 73858-59-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Pyrrolidinylphosphonic Acid is used as an impurity in the production of Alendronate (A521250) for its role as a bone reabsorption inhibitor. Alendronate is a medication prescribed to treat and prevent osteoporosis, as well as other conditions that involve the weakening of bones. The presence of 2-Pyrrolidinylphosphonic Acid in the manufacturing process may affect the efficacy and safety of the final product, making its control and management crucial in the pharmaceutical industry.

Upstream product

• 73858-58-9 (+/-)-diethyl pyrrolidine-2-phosphonate 
• 345229-22-3 Pyrrolidin-2-phosphonsaeurediphenylester 
• 347386-53-2 tert-butyl 2-(dimethoxyphosphoryl)pyrrolidine-1-carboxylate 
• 762-04-9 Diethyl phosphonate 
• 869855-90-3 dimethyl pyrrolidine-2-phosphonate 

Relevant articles and documents

Conversion of nitriles to 1-aminophosphonic acids and preparation of phosphahomocysteines of high enantiomeric excess

A variety of nitriles was reduced to diisobutylaluminum salts of aldimines, to which diisopropyl phosphite was added. The corresponding 1-aminophosphonates were either deprotected to give racemic 1-aminophosphonic acids or reacted with Boc2O to yield N-Boc-protected 1-aminophosphonates. The enantiomers of 2-benzylthio-1-(t-butoxycarbonylamino)propylphosphonate were obtained from the racemate by chiral HPLC and converted to phosphonic acid analogs of (R)- and (S)-homocysteine, (R)- and (S)-2-aminobutyric acid and (S)-methionine, all of ee >97% as determined by chiral HPLC.

Chemical conversion of cyclic α-amino acids to cyclic α-aminophosphonic acids

The oxidative decarboxylation of cyclic α-amino acids having urethane-type N-protecting groups with lead tetraacetate [Pb(OAc)4] gave 2-hydroxy derivatives, which were transformed into the corresponding α-aminophosphonic acid esters by treatment of trialkyl phosphites in the presence of Lewis acids. Deprotection and ester cleavage of the products in the usual manner afforded cyclic α-aminophosphonic acids. The convenient chemical conversion of five- and six-membered cyclic α-amino acids to the corresponding cyclic α-aminophosphonic acids has been accomplished.

PHOSPHONIC ANALOGS OF PROLINE

A method of synthesis of phosphonic analogs of proline and its P-methyl and P-phenyl derivatives has been developed.