Ephedroxane

Base Information

• Chemical Name: Ephedroxane
• CAS No.: 16251-46-0
• Molecular Formula: C11H13 N O2
• Molecular Weight: 191.23
• DSSTox Substance ID: DTXSID80167382
• Nikkaji Number: J33.905I
• Wikidata: Q27155310
• Mol file: 16251-46-0.mol

Synonyms:ephedroxane;ephedroxane, (4R-cis)-isomer;ephedroxane, (4R-trans)-isomer;ephedroxane, (4S-trans)-isomer;ephedroxane, (cis-(+-))-isomer;ephedroxane, (trans-(+-))-isomer;pseudoephedroxane

Chemical Property of Ephedroxane

Chemical Property:

• Vapor Pressure: 1.12E-05mmHg at 25°C
• Boiling Point: 370.3°Cat760mmHg
• Flash Point: 177.8°C
• PSA: 29.54000
• Density: 1.115g/cm³
• LogP: 2.13610
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 191.094628657
• Heavy Atom Count: 14
• Complexity: 223

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(OC(=O)N1C)C2=CC=CC=C2
• Isomeric SMILES: C[C@H]1[C@H](OC(=O)N1C)C2=CC=CC=C2

Technology Process of Ephedroxane

There total 32 articles about Ephedroxane 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: 79.0%

3-Methyl-4-methyl-5-phenyl-4-oxazolin-2-one (54026-27-6) → (4RS,5SR)-3,4-dimethyl-5-phenyloxazolidin-2-one (6317-31-3,15833-15-5,16251-46-0,16251-47-1,32461-36-2,32461-37-3,91049-48-8,91049-51-3,91740-65-7)

Guidance literature:

With hydrogen; platinum(IV) oxide; In acetic acid; for 0.5h;

DOI:10.1016/S0040-4039(00)85960-2

Reference yield: 72.0%

(4RS,5SR)-3-methyl-4-(4-methylphenylsulfonyloxymethyl)-5-phenyloxazolidin-2-one → (4RS,5SR)-3,4-dimethyl-5-phenyloxazolidin-2-one (6317-31-3,15833-15-5,16251-46-0,16251-47-1,32461-36-2,32461-37-3,91049-48-8,91049-51-3,91740-65-7)

Guidance literature:

With sodium tetrahydroborate; In dimethyl sulfoxide; at 150 ℃; for 2h;

DOI:10.1021/jo9819988

Reference yield: 70.0%

BOC-pseudoephedrine (152614-95-4) → (4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one (16251-46-0)

Guidance literature:

With p-toluenesulfonyl chloride; In pyridine; RT, 4 d; reflux, 1 h;

upstream raw materials:

phosgene

ephedrine

ephedrine hydrochloride

urea

Downstream raw materials:

methamphetamin

(+/-)-N-methylephedrine

ephedrine

Refernces

• 1、 Schulze, Matthias. "Synthesis of 2-Arylethylamines by the Curtius Rearrangement". experimental part. p. 1461 - 1476. Retrieved 2010/07/08.
• 2、 Hamdach,El Hadrami,Gil,Zaragozá,Zaballos-García,Sepúlveda-Arques. "Reactivity difference between diphosgene and phosgene in reaction with (2,3-anti)-3-amino-1,2-diols". . p. 6392 - 6397. Retrieved 2007/10/03.