(R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine

Base Information

• Chemical Name: (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine
• CAS No.: 608142-27-4
• Molecular Formula: C12H19NO4S
• Molecular Weight: 273.353
• European Community (EC) Number: 864-867-4
• Mol file: 608142-27-4.mol

Synonyms:608142-27-4;(R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine;(R)-1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine;(1R)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethanamine;(R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethan-1-amine;SCHEMBL753579;BXUJVINGXQGNFD-JTQLQIEISA-N;AKOS028113321;BS-51422;E80514;A930223;(1R)-1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonyl-ethylamine;(1R)-1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethan-1-amine

Chemical Property of (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine

Chemical Property:

• Boiling Point: 469.6±45.0 °C(Predicted)
• PKA: 6.84±0.10(Predicted)
• PSA: 87.00000
• Density: 1.195±0.06 g/cm3(Predicted)
• LogP: 2.91940
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 273.10347926
• Heavy Atom Count: 18
• Complexity: 339

Purity/Quality:

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

(αR)?-3-?Ethoxy-?4-?methoxy-?α-?[(methylsulfonyl)?methyl]?-benzenemethanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=C(C=CC(=C1)C(CS(=O)(=O)C)N)OC
• Isomeric SMILES: CCOC1=C(C=CC(=C1)[C@H](CS(=O)(=O)C)N)OC
• Uses: (αR)?-3-?Ethoxy-?4-?methoxy-?α-?[(methylsulfonyl)?methyl]?-benzenemethanamine is a reagent used in the synthesis of Apremilast, a potent and active tumor necrosis factor inhibitor.

Technology Process of (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine

There total 16 articles about (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine 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: 70.0%

1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethen-1-amine (1450657-31-4) → (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)-ethylamine (608142-27-4)

Guidance literature:

With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene; hydrogen; In 2,2,2-trifluoroethanol; at 50 ℃; for 18h; under 5414.51 Torr; Reagent/catalyst; Pressure; Inert atmosphere;

Reference yield: 45.0%

2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine (253168-94-4) → (S)-2-[1 (3-ethoxy-4-methoxyphenyl)]-1-methanesulfonyl-2-ethylamine (608141-42-0) + (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)-ethylamine (608142-27-4)

Guidance literature:

2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine; With N-Ac-Leu; In methanol;

With sodium hydroxide;

DOI:10.1002/cctc.201901473

Reference yield:

1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethen-1-amine (1450657-31-4) → (S)-2-[1 (3-ethoxy-4-methoxyphenyl)]-1-methanesulfonyl-2-ethylamine (608141-42-0) + (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)-ethylamine (608142-27-4)

Guidance literature:

With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-[bis[4-(trifluoromethyl)phenyl]phosphino]ferrocene; hydrogen; In 2,2,2-trifluoroethanol; at 50 ℃; for 18h; under 13689.1 Torr; Reagent/catalyst; Solvent; Temperature; Time; Inert atmosphere;

upstream raw materials:

2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine

isovanillin

3-ethoxy-4-methoxybenzaldehyde

(R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethylamine N-acetyl-D-leucine salt

Downstream raw materials:

R-Apremilast

4-amino-2-[(1S)-1-(3-ethoxy 4-methoxyphenyl)-2-methanesulfonylethyl]-2,3-dihydro-1H-isoindole-1,3-dione

Apremilast

(S)-2-[1 (3-ethoxy-4-methoxyphenyl)]-1-methanesulfonyl-2-ethylamine

Refernces

• 1、 Jana, Anupam,Zieliński, Grzegorz Krzysztof,Czarnocka-?niada?a, Sylwia,Grudzień, Krzysztof,Podwysocka, Dominika,Szulc, Marcin,Kajetanowicz, Anna,Grela, Karol. "Synthesis of Substituted β-Functionalised Styrenes by Microwave-Assisted Olefin Cross-Metathesis and Scalable Synthesis of Apremilast". . p. 5808 - 5813. Retrieved 2019/11/03.
• 2、 -. "A METHOD OF CHIRAL RESOLUTION OF THE KEY INTERMEDIATE OF THE SYNTHESIS OF APREMILAST AND ITS USE FOR THE PREPARATION OF PURE APREMILAST". Page/Page column 22. . Retrieved 2016/10/31.