[3H](R)-(-)-baclofen

Base Information

• Chemical Name: [3H](R)-(-)-baclofen
• CAS No.: 69308-37-8
• Molecular Formula: C10H12 Cl N O2
• Molecular Weight: 213.664
• Mol file: 69308-37-8.mol

Synonyms:[3H](R)-(-)-baclofen;D0H5JW

Chemical Property of [3H](R)-(-)-baclofen

Chemical Property:

• Vapor Pressure: 6.01E-06mmHg at 25°C
• Melting Point: 171-174°C
• Refractive Index: 1.576
• Boiling Point: 364.3 °C at 760 mmHg
• PKA: 4.04±0.10(Predicted)
• Flash Point: 174.1 °C
• PSA: 63.32000
• Density: 1.285g/cm³
• LogP: 2.55730
• Storage Temp.: Store at RT
• Water Solubility.: Practically insoluble in water
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 213.0556563
• Heavy Atom Count: 14
• Complexity: 185

Purity/Quality:

99% ^*data from raw suppliers

(R)-Baclofen ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(CC(=O)[O-])C[NH3+])Cl
• Isomeric SMILES: C1=CC(=CC=C1[C@@H](CC(=O)[O-])C[NH3+])Cl
• Uses: (R)-baclofen is a derivative of gamma-aminobutyric acid primarily used to treat spasticity. R-Enantiomer of Baclofen. Specific GABA-B receptor agonist. Muscle relaxant (skeletal).

Technology Process of [3H](R)-(-)-baclofen

There total 56 articles about [3H](R)-(-)-baclofen 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%

(R)-2-[(R)-4-(4-Chloro-phenyl)-4,5-dihydro-3H-pyrrol-2-ylamino]-2-phenyl-ethanol (185761-27-7) → (R)-baclofen (69308-37-8)

Guidance literature:

With sodium hydroxide; ethanol; at 100 ℃; for 14h;

DOI:10.1016/S0040-4020(96)00946-5

Reference yield: 91.0%

(R)-(-)-baclofen hydrochloride (63701-55-3,70206-22-3) → (R)-baclofen (69308-37-8)

Guidance literature:

With sodium hydroxide; In water; pH=6.5 - 7; Product distribution / selectivity;

Reference yield: 80.0%

(R)-(-)-3-(4-chloro-phenyl)-4-nitro-butyric acid (290366-79-9) → (R)-baclofen (69308-37-8)

Guidance literature:

With hydrogen; nickel; In ethanol; under 760 Torr;

DOI:10.1016/j.tetasy.2005.02.019

upstream raw materials:

(R)-2-[(R)-4-(4-Chloro-phenyl)-4,5-dihydro-3H-pyrrol-2-ylamino]-2-phenyl-ethanol

(E)-(S)-3-(4-Chloro-phenyl)-hex-4-enoic acid ethyl ester

1-[(3S)-3-(4-chlorophenyl)cyclobut-1-enyloxyl]-1,1-diethyl-1-silapropane

(R)-ethyl 4-[(tert-butoxycarbonyl)amino]-3-(4-chlorophenyl)butanoate

Downstream raw materials:

(3R)-4-{[(1R)-2-methyl-1-(2-methylpropanoyloxy)propoxy]carbonylamino}-3-(4-chlorophenyl)butanoic acid

[3H]-Arbaclofen placarbil

(R)-(-)-4-(4-chlorophenyl)pyrrolidin-2-one

(R)-4-(4-chloro-3-iodophenyl)pyrrolidin-2-one

Refernces

HClO₄·SiO₂-mediated improved isomerization of glycidic esters to α-hydroxy-β,γ -unsaturated esters: Application in the formal synthesis of (R)-Baclofen and β-phenyl GABA analogues

10.1246/cl.2012.325

The research focuses on the isomerization of glycidic esters to β-hydroxy-α,ω-unsaturated esters (allylic alcohols) using HClO4·SiO2 as an efficient catalyst. This method was applied in the formal synthesis of (R)-Baclofen and α-phenyl GABA analogues. The study found that HClO4·SiO2 is a stable and effective reagent for this transformation, yielding allylic alcohols in good to high yields. These allylic alcohols were then converted into GABA derivatives through selective SN2 nucleophilic substitution with azide ion, followed by hydrogenation and reduction steps. The key chemicals involved in this research include glycidic esters derived from various ketones, HClO4·SiO2 as the catalyst, azide ion for the nucleophilic substitution, and palladium on carbon (Pd/C) for hydrogenation. The study also utilized methanesulfonyl chloride (MsCl) and sodium azide (NaN3) in the conversion process. The results demonstrate a new and efficient route for synthesizing important GABA derivatives, such as Baclofen, using readily available reagents and mild reaction conditions.