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

Base Information

• Chemical Name: (1S,2S)-Pseudoephedrine-(R)-2-methylhydrocinnamamide
• CAS No.: 159345-06-9
• Molecular Formula: C20H25 N O2
• Molecular Weight: 311.424
• DSSTox Substance ID: DTXSID90446599
• Nikkaji Number: J876.954K
• Wikidata: Q82265307
• Mol file: 159345-06-9.mol

Synonyms:159345-06-9;(1S,2S)-Pseudoephedrine-(R)-2-methylhydrocinnamamide;(2R)-N-[(1S,2S)-1-HYDROXY-1-PHENYLPROPAN-2-YL]-N,2-DIMETHYL-3-PHENYLPROPANAMIDE;DTXSID90446599;YBSOZNKAYZZSLZ-JTDSTZFVSA-N;AKOS015913094;(1S,2S)-Pseudoephedrine-(R)-2-methylhydrocinnamamide, 97%;(1S,2S)-2-[Methyl[(R)-2-methyl-3-phenylpropanoyl]amino]-1-phenyl-1-propanol

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

Chemical Property:

• Vapor Pressure: 3.71E-10mmHg at 25°C
• Melting Point: 136-140 °C(lit.)
• Refractive Index: 1.567
• Boiling Point: 483.4°C at 760 mmHg
• PKA: 13.70±0.20(Predicted)
• Flash Point: 246.2°C
• PSA: 40.54000
• Density: 1.091g/cm³
• 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:

99% ,98%,Electron Grade , ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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

There total 3 articles about (1S,2S)-Pseudoephedrine-(R)-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: 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

Reference yield: 70.0%

potassium (R)-3-(trifluoroborato)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpropanamide + chlorobenzene (108-90-7) → (2R)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethyl-3-phenylpropionamide (159345-06-9,352530-53-1)

Guidance literature:

With palladium diacetate; potassium carbonate; ruphos; In water; toluene; at 85 ℃; for 22h; Inert atmosphere;

DOI:10.1021/ol101865e

Reference yield:

pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) → (2R)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethyl-3-phenylpropionamide (159345-06-9,352530-53-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 23 °C

2: 90 percent / LiCl, diisopropylamine, n-BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C

With n-butyllithium; triethylamine; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/ja970402f

upstream raw materials:

benzyl bromide

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

pseudoephedrine

chlorobenzene

Downstream raw materials:

(2R)-2-methyl-1-phenylheptan-3-one

(2R)-1,3-diphenyl-2-methyl-propan-1-one

(2S)-2-methyl-3-phenylpropanal

(2R)-2-methyl-3-phenylpropanal