Dexoxadrol

Base Information

• Chemical Name: Dexoxadrol
• CAS No.: 4741-41-7
• Deprecated CAS: 47255-55-0
• Molecular Formula: C22H28ClNO2
• Molecular Weight: 309.408
• UNII: JY5N9F45AG
• DSSTox Substance ID: DTXSID50912321
• Nikkaji Number: J8.768H
• Wikipedia: Dexoxadrol
• Wikidata: Q5268344
• NCI Thesaurus Code: C65372
• ChEMBL ID: CHEMBL1165411
• Mol file: 4741-41-7.mol

Synonyms:d-2,2-Diphenyl-4-(2-piperidyl)-1,3-dioxolane;dexoxadrol;dexoxadrol hydrochloride

Chemical Property of Dexoxadrol

Chemical Property:

• Vapor Pressure: 5.26E-08mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 441.9°C at 760 mmHg
• Flash Point: 187.1°C
• PSA: 30.49000
• Density: 1.13g/cm³
• LogP: 3.77400
• Water Solubility.: 70mg/L(room temperature)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 309.172878976
• Heavy Atom Count: 23
• Complexity: 356

Purity/Quality:

99% ^*data from raw suppliers

DEXOXADROL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCNC(C1)C2COC(O2)(C3=CC=CC=C3)C4=CC=CC=C4
• Isomeric SMILES: C1CCN[C@@H](C1)[C@H]2COC(O2)(C3=CC=CC=C3)C4=CC=CC=C4
• Uses: Stimulant (central); analgesic.

Technology Process of Dexoxadrol

There total 5 articles about Dexoxadrol 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: 99.0%

benzyl (2S)-2-[(4S)-2,2-diphenyl-1,3-dioxolan-4-yl]-1,2,3,6-tetrahydropyridine-1-carboxylate (1247664-50-1) → dexoxadrol (4741-41-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; under 760.051 Torr;

DOI:10.1055/s-0030-1258110

Reference yield: 60.0%

dimethoxydiphenylmethane (2235-01-0) + (βS,2S)-β-hydroxypiperidin-2-ethanol (117994-55-5) → dexoxadrol (4741-41-7)

Guidance literature:

With toluene-4-sulfonic acid; In isopropyl alcohol; for 1h; Reflux;

DOI:10.1016/j.tet.2013.10.082

Reference yield:

benzyl (2S,4R)-2-[(4S)-2,2-diphenyl-1,3-dioxolan-4-yl]-4-hydroxypiperidine-1-carboxylate (1257901-09-9) → WMS-2539 (1257844-26-0) + dexoxadrol (4741-41-7)

Guidance literature:

benzyl (2S,4R)-2-[(4S)-2,2-diphenyl-1,3-dioxolan-4-yl]-4-hydroxypiperidine-1-carboxylate; With diethylamino-sulfur trifluoride; In dichloromethane; at -78 ℃; for 3h; Inert atmosphere;

With 10% palladium on activated carbon; hydrogen; In methanol; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.bmc.2010.09.047

upstream raw materials:

benzyl (2S)-2-[(4S)-2,2-diphenyl-1,3-dioxolan-4-yl]-1,2,3,6-tetrahydropyridine-1-carboxylate

benzyl (2S,4R)-2-[(4S)-2,2-diphenyl-1,3-dioxolan-4-yl]-4-hydroxypiperidine-1-carboxylate

(S)-benzyl-2-vinylpiperidine-1-carboxylate

dimethoxydiphenylmethane

Downstream raw materials:

Epietoxadrol hydrochloride

Etoxadrol hydrochloride

(+)-dexoxadrol hydrochloride

Refernces

• 1、 Etayo, Pablo,Badorrey, Ramón,Díaz-De-Villegas, María D.,Gálvez, José A.,López-Ram-De-Víu, Pilar. "An expeditious method for the first asymmetric synthesis of dexoxadrol from the chiral pool". experimental part. p. 1775 - 1778. Retrieved 2010/10/20.