(2R,5R)-2,5-dimethyl-1-[(4-methylphenyl)sulfonyl]pyrrolidine

Base Information

• Chemical Name: (2R,5R)-2,5-dimethyl-1-[(4-methylphenyl)sulfonyl]pyrrolidine
• CAS No.: 123993-97-5
• Molecular Formula: C13H19 N O2 S
• Molecular Weight: 253.3605
• Mol file: 123993-97-5.mol

Synonyms:Pyrrolidine,2,5-dimethyl-1-[(4-methylphenyl)sulfonyl]-, trans- (9CI); Pyrrolidine, 2,5-dimethyl-1-[(4-methylphenyl)sulfonyl]-,trans-(?à)-

Chemical Property of (2R,5R)-2,5-dimethyl-1-[(4-methylphenyl)sulfonyl]pyrrolidine

Chemical Property:

• Vapor Pressure: 1.68E-05mmHg at 25°C
• Boiling Point: 364.5°C at 760 mmHg
• Flash Point: 174.2°C
• Density: 1.134g/cm³

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,5R)-2,5-dimethyl-1-[(4-methylphenyl)sulfonyl]pyrrolidine

There total 21 articles about (2R,5R)-2,5-dimethyl-1-[(4-methylphenyl)sulfonyl]pyrrolidine 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: 48.0%

N-(1-methylpent-4-en-1-yl)(4-methylphenyl)sulfonamide (898832-97-8) → (+/-)-cis-3,8-dimethyl-2,3,10,10a-tetrahydro-1H-pyrrolo[1,2-b][1,2]benzothiazine-5,5-dioxide + (+/-)-trans-3,8-dimethyl-2,3,10,10a-tetrahydro-1H-pyrrolo[1,2-b][1,2]benzothiazine-5,5-dioxide + cis-N-(p-toluenesulfonyl)-2,5-dimethylpyrrolidine (81330-01-0) + trans-N-(p-toluenesulfonyl)-2,5-dimethylpyrrolidine (123993-97-5)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 210 ℃; for 3h; microwave irradiation;

DOI:10.1021/jo070321u

Reference yield:

1,5-Hexadien (592-42-7) + toluene-4-sulfonamide (70-55-3) → cis-N-(p-toluenesulfonyl)-2,5-dimethylpyrrolidine (81330-01-0) + trans-N-(p-toluenesulfonyl)-2,5-dimethylpyrrolidine (123993-97-5)

Guidance literature:

With (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate; In toluene; at 95 ℃; Title compound not separated from byproducts;

DOI:10.1021/ja053864z

Reference yield:

sodium p-toluenesulfonamide (18522-92-4) → trans-N-(p-toluenesulfonyl)-2,5-dimethylpyrrolidine (123993-97-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / Cs₂C₁O₃ / dimethylformamide / 48 h / 50 °C

2: aqueous NaOH / methanol / 0.75 h / Heating

3: H₂ / PtO₂ / methanol / 3 h / 3800 Torr / Ambient temperature

4: triethylamine / tetrahydrofuran / 1) 0 deg C, 1.5 h, 2) RT, 1 h

5: K₂CO₃ / methanol / 3 h / Ambient temperature

With sodium hydroxide; Cs₂C₁O₃; hydrogen; potassium carbonate; triethylamine; platinum(IV) oxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00290a010

upstream raw materials:

(R*,S*)-2-(mesyloxy)-5-(p-toluenesulfonamido)hexane

Methanesulfonic acid (1R,4R)-1-methyl-4-(toluene-4-sulfonylamino)-pentyl ester

1,5-Hexadien

toluene-4-sulfonamide