(1R, 2R)-Pseudoephedrine-(S)-2-methylhydrocinnamamide

Base Information

• Chemical Name: (1R, 2R)-Pseudoephedrine-(S)-2-methylhydrocinnamamide
• CAS No.: 352530-53-1
• Molecular Formula: C₂₀H₂₅NO₂
• Molecular Weight: 311.424
• DSSTox Substance ID: DTXSID30478253
• Wikidata: Q82311501
• Mol file: 352530-53-1.mol

Synonyms:(1R, 2R)-Pseudoephedrine-(S)-2-methylhydrocinnamamide;352530-53-1;DTXSID30478253;(1R, 2R)-Pseudoephedrine-(S)-2-methylhydrocinnamamide, 97%

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Chemical Property of (1R, 2R)-Pseudoephedrine-(S)-2-methylhydrocinnamamide

Chemical Property:

• Vapor Pressure: 5.86E-12mmHg at 25°C
• Melting Point: 136-140 °C(lit.)
• Boiling Point: 527.6°C at 760 mmHg
• PKA: 13.70±0.20(Predicted)
• Flash Point: 272.9°C
• PSA: 40.54000
• Density: 1.091±0.06 g/cm3(Predicted)
• LogP: 3.44570
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 311.188529040
• Heavy Atom Count: 23
• Complexity: 359

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CC1=CC=CC=C1)C(=O)N(C)C(C)C(C2=CC=CC=C2)O
• Isomeric SMILES: C[C@@H](CC1=CC=CC=C1)C(=O)N(C)[C@H](C)[C@@H](C2=CC=CC=C2)O

Technology Process of (1R, 2R)-Pseudoephedrine-(S)-2-methylhydrocinnamamide

There total 13 articles about (1R, 2R)-Pseudoephedrine-(S)-2-methylhydrocinnamamide 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%

C13H17NO2(2-)*2Na(1+) + benzyl bromide (100-39-0) → N-(2-hydroxy-1-methyl-2-phenyl-ethyl)-2,N-dimethyl-3-phenyl-propionamide (352530-53-1)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 0.166667h; stereoselective reaction;

DOI:10.1021/jacs.9b08176

Reference yield: 95.0%

N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-3-phenylpropanamide (14980-86-0,42407-58-9) + methyl iodide (74-88-4) → (S)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethyl-3-phenylpropanamide (159345-08-1,352530-53-1)

Guidance literature:

With n-butyllithium; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; at -78 ℃;

DOI:10.1021/ja970402f

Reference yield: 90.0%

benzyl bromide (100-39-0) + N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide (159213-03-3) → (2R)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethyl-3-phenylpropionamide (159345-06-9,352530-53-1)

Guidance literature:

With lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃;

DOI:10.1055/s-1997-6121

upstream raw materials:

benzyl bromide

N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide

pseudoephedrine

chlorobenzene

Downstream raw materials:

(2R,3R)-2-methyl-1-phenyl-hex-5-en-3-ol

Refernces

• 1、 Zhou, Yuhui,Keresztes, Ivan,Macmillan, Samantha N.,Collum, David B.. "Disodium Salts of Pseudoephedrine-Derived Myers Enolates: Stereoselectivity and Mechanism of Alkylation". . p. 16865 - 16876. Retrieved 2019/11/03.
• 2、 Hutchison, Panee C.,Heightman, Tom D.,Procter, David J.. "Application of A Recyclable Pseudoephedrine Resin in Asymmetric Alkylations on Solid Phase". . p. 790 - 801. Retrieved 2007/10/03.