(2R)-Pyrrolidinium-2beta-methanol

Base Information

• Chemical Name: (2R)-Pyrrolidinium-2beta-methanol
• CAS No.: 68832-13-3
• Molecular Formula: C5H11NO
• Molecular Weight: 101.148
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID00988536
• Nikkaji Number: J2.679.359I
• Mol file: 68832-13-3.mol

Synonyms:DTXSID00988536;(2R)-Pyrrolidinium-2beta-methanol;2-(Hydroxymethyl)pyrrolidin-1-ium

Chemical Property of (2R)-Pyrrolidinium-2beta-methanol

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 0.0423mmHg at 25°C
• Refractive Index: n20/D 1.485
• Boiling Point: 211 °C at 760 mmHg
• PKA: 14.77±0.10(Predicted)
• Flash Point: 86.1 °C
• PSA: 32.26000
• Density: 0.978 g/cm³
• LogP: 0.05950
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Chloroform (Slightly), Methanol (Slightly), Toluene (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 102.091889006
• Heavy Atom Count: 7
• Complexity: 56

Purity/Quality:

99% ^*data from raw suppliers

D-Prolinol ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC([NH2+]C1)CO
• Isomeric SMILES: C1C[C@@H]([NH2+]C1)CO
• Uses: (2R)-2-Pyrrolidinemethanol is used in the synthesis of potent selective 5-HT7 antagonists.

Technology Process of (2R)-Pyrrolidinium-2beta-methanol

There total 3 articles about (2R)-Pyrrolidinium-2beta-methanol 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:

N-acetyl-L-phenylalanyl-L-prolinol → D-prolinol (68832-13-3) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6)

Guidance literature:

With water;

DOI:10.1038/s41429-018-0041-3

Reference yield:

L-(-)Prolin (147-85-3,344-25-2,609-36-9,7005-20-1,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (+)-2-hydroxymethylpyrrolidine (498-63-5,10200-26-7,23356-96-9,68832-13-3)

Guidance literature:

With lithium aluminium tetrahydride;

DOI:10.1016/S0040-4039(01)93014-X

Reference yield:

1-(aminoiminomethyl)-prolinol N,N-dimethylvaline ester → (R)-2-(N,N-dimethylamino)-3-methylbutanoic acid (899900-52-8) + D-prolinol (68832-13-3)

Guidance literature:

With sodium hydroxide; at 100 ℃; for 3h;

DOI:10.3390/md19080413

upstream raw materials:

L-(-)Prolin

Downstream raw materials:

(2R)-(+)-phenylmethyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate

2-methoxy-1-<<2(S)-(hydroxymethyl)pyrrolidinyl>carbonyl>benzene

(R)-2-hydroxymethyl-N-(3-phenyl-2-propynoyl)pyrrolidine

(R)-1-aza-3-oxobicyclo<3.3.0>octan-2-one

Refernces

Discovery and optimization of (R)-prolinol-derived agonists of the Growth Hormone Secretagogue receptor (GHSR)

10.1016/j.bmcl.2008.07.120

The research focuses on the discovery and optimization of (R)-prolinol-derived agonists for the Growth Hormone Secretagogue receptor (GHSR), a G-protein-coupled receptor involved in growth, metabolism, and food intake regulation. The study utilized a solid-phase library of 11,520 members targeting the GPCR protein superfamily, employing solid-phase synthesis and matrix libraries to rapidly optimize low micromolar hits into single-digit nanomolar leads. The research revealed non-additive structure-activity relationships and the significant impact of the α-methyl stereochemistry on GHSR activity. Reactants included cyclic and acyclic secondary amino alcohols, primary amines, anilines, and carboxylic acids, while analyses involved HPLC, mass spectrometry, and 1H NMR to ensure purity and characterize compounds. The experiments led to the identification of potent GHSR agonists with potential clinical applications in treating growth hormone disorders, frailty, and cachexia.