(2R,5R)-1-Benzyl-2,5-dimethylpyrrolidine

Base Information

• Chemical Name: (2R,5R)-1-Benzyl-2,5-dimethylpyrrolidine
• CAS No.: 119008-53-6
• Molecular Formula: C₁₃H₁₉N
• Molecular Weight: 189.301
• DSSTox Substance ID: DTXSID10446394
• Mol file: 119008-53-6.mol

Synonyms:119008-53-6;(2R,5R)-1-Benzyl-2,5-dimethylpyrrolidine;(2R,5R)-N-Benzyl-2,5-dimethylpyrrolidine;(-)-N-BENZYL-(2R,5R)-2,5-DIMETHYLPYRROLIDINE;rel-(2R,5R)-1-Benzyl-2,5-dimethylpyrrolidine;Pyrrolidine, 2,5-dimethyl-1-(phenylmethyl)-, (2R,5R)-;4209-71-6;starbld0008323;(2R,5R)-2,5-Dimethyl-1-(phenylmethyl)pyrrolidine;DTXSID10446394;AKOS006278033;J-004049

Chemical Property of (2R,5R)-1-Benzyl-2,5-dimethylpyrrolidine

Chemical Property:

• Vapor Pressure: 0.0229mmHg at 25°C
• Boiling Point: 249.5°C at 760 mmHg
• Flash Point: 95.6°C
• PSA: 3.24000
• Density: 0.955g/cm³
• LogP: 2.99730
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 189.151749610
• Heavy Atom Count: 14
• Complexity: 162

Purity/Quality:

98%Min ^*data from raw suppliers

(2R,5R)-N-Benzyl-2,5-dimethylpyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(N1CC2=CC=CC=C2)C
• Isomeric SMILES: C[C@@H]1CC[C@H](N1CC2=CC=CC=C2)C
• Uses: (2R,5R)-N-Benzyl-2,5-dimethylpyrrolidine is a reagent used for asymmetric syntheses.

Technology Process of (2R,5R)-1-Benzyl-2,5-dimethylpyrrolidine

There total 5 articles about (2R,5R)-1-Benzyl-2,5-dimethylpyrrolidine 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: 86.0%

benzylamine (100-46-9) + (4S,7S)-4,7-dimethyl-1,3,2-dioxathiepane 2,2-dioxide (220224-82-8) → (-)-N-benzyl-(2R,5R)-2,5-dimethylpyrrolidine (119008-53-6)

Guidance literature:

at 20 ℃; for 96h;

DOI:10.1071/CH03238

Reference yield:

(2S,5S)-2,5-hexanediol (34338-96-0) → (-)-N-benzyl-(2R,5R)-2,5-dimethylpyrrolidine (119008-53-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / CH₂Cl₂ / 18 h / 20 °C

2: 87 percent / thionyl chloride / CCl₄ / 1 h / Heating

3: 65 percent / RuCl₃; sodium periodate / CCl₄; acetonitrile; H₂O / 1 h / 25 °C

4: 86 percent / 96 h / 20 °C

With ruthenium trichloride; sodium periodate; thionyl chloride; In tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1071/CH03238

Reference yield:

(4S,7S)-4,7-Dimethyl-[1,3,2]dioxathiepane 2-oxide (750635-93-9) → (-)-N-benzyl-(2R,5R)-2,5-dimethylpyrrolidine (119008-53-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / RuCl₃; sodium periodate / CCl₄; acetonitrile; H₂O / 1 h / 25 °C

2: 86 percent / 96 h / 20 °C

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile;

DOI:10.1071/CH03238

upstream raw materials:

(S,S)-2,5-bis(methylsulfonyloxy)hexane

benzylamine

(4S,7S)-4,7-dimethyl-1,3,2-dioxathiepane 2,2-dioxide

(4S,7S)-4,7-Dimethyl-[1,3,2]dioxathiepane 2-oxide

Downstream raw materials:

(2R,5R)-2,5-dimethyltetrahydro-1H-1-pyrrolylidium chloride

2-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]ethanol