3-Hydroxypyrrolidin-1-ium

Base Information

• Chemical Name: 3-Hydroxypyrrolidin-1-ium
• CAS No.: 100243-39-8
• Molecular Formula: C4H9NO
• Molecular Weight: 87.1216
• Hs Code.: DERIVATION
• DSSTox Substance ID: DTXSID70905295
• Wikidata: Q72481663
• Mol file: 100243-39-8.mol

Synonyms:3-Hydroxypyrrolidin-1-ium;DTXSID70905295

Chemical Property of 3-Hydroxypyrrolidin-1-ium

Chemical Property:

• Appearance/Colour: Clear light yellow to yellow liquid after melting
• Vapor Pressure: 0.018mmHg at 25°C
• Melting Point: 15 °C
• Refractive Index: 1.487 - 1.491
• Boiling Point: 224.7 °C at 760 mmHg
• PKA: 14.91±0.20(Predicted)
• Flash Point: 105.8 °C
• PSA: 32.26000
• Density: 1.078 g/cm³
• LogP: -0.33060
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive & Hygroscopic
• Water Solubility.: Fully miscible in water.
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 88.076238942
• Heavy Atom Count: 6
• Complexity: 46.8

Purity/Quality:

99%, ^*data from raw suppliers

(S)-3-Hydroxypyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-40
• Safety Statements: 26-37/39-36-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C[NH2+]CC1O
• Isomeric SMILES: C1C[NH2+]C[C@H]1O
• Uses: (S)-(-)-3-Hydroxypyrrolidine is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuff fields.

Technology Process of 3-Hydroxypyrrolidin-1-ium

There total 27 articles about 3-Hydroxypyrrolidin-1-ium 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: 100.0%

(S)-N-benzyl-3-hydroxypyrrolidine (101385-90-4) → 3-hydroxypyrrolidine (100243-39-8)

Guidance literature:

With 20% palladium hydroxide-activated charcoal; hydrogen; In methanol;

DOI:10.3998/ark.5550190.p008.210

Reference yield: 98.0%

(R)-N-benzyl-3-hydroxypyrrolidine (101385-90-4,101930-07-8,101979-03-7,775-15-5) → (3R)-pyrrolidinol (40499-83-0,83220-72-8,100243-39-8,2799-21-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 2h;

DOI:10.1271/bbb.59.1287

Reference yield: 93.0%

4R-4-hydroxyproline (51-35-4,30724-02-8) → (3R)-pyrrolidinol (40499-83-0,83220-72-8,100243-39-8,2799-21-5)

Guidance literature:

cyclohexenone; In various solvent(s); at 154 ℃; for 2h;

DOI:10.1246/cl.1986.893

upstream raw materials:

(3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione

4R-4-hydroxyproline

(R)-N-benzyl-3-hydroxypyrrolidine

(4R)-4-hydroxyproline

Downstream raw materials:

(R)-1-(3-hydroxypyrrolidin-1-yl)ethan-1-one

(R)-1-(2-methoxyethyl)-3-hydroxypyrrolidine

(R)-1-(o-methoxyphenylmethyl)-3-hydroxypyrrolidine

(R)-N-(p-nitrophenyl)-3-hydroxypyrrolidine

Refernces

• 1、 Mehler,Martens,Wallbaum. "Enantioselective addition of diethylzinc to aromatic aldehydes catalysed by chiral ligands derived from L-hydroxyproline". . p. 2691 - 2699. Retrieved 1993.
• 2、 Horiguchi,Mochida. "Enzymatic optical resolution of N-benzyl-3-pyrrolidinol". . p. 1287 - 1290. Retrieved 1995.
• 3、 Klein, Scott I.,Czekaj, Mark,Molino, Bruce F.,Valeria, Chu. "Constrained β-alanine based GpIIb/IIIa antagonists". . p. 1773 - 1778. Retrieved 1997.
• 4、 Wallbaum,Mehler,Martens. "Decarboxylation of α-amino acids containing two and three stereogenic centers: A simple one-step procedure to prepare two optically active β- amino alcohols and a bicyclic pyrrolidine derivative". . p. 1381 - 1387. Retrieved 1994.
• 5、 -. "Synthesis method of (R)-3-hydroxypyrrolidine". Paragraph 0021-0026. . Retrieved 2021/04/17.
• 6、 -. "A fang chanfu law compound and its preparation method, pharmaceutical composition and use thereof". Paragraph 0022; 0023; 0024; 0025; 0026. . Retrieved 2018/03/02.