1-Methyl-2β-benzyl-5β-nonylpyrrolidine-3β-ol

Base Information

• Chemical Name: 1-Methyl-2β-benzyl-5β-nonylpyrrolidine-3β-ol
• CAS No.: 125356-66-3
• Molecular Formula: C21H35 N O
• Molecular Weight: 317.515
• Mol file: 125356-66-3.mol

Synonyms:3-Pyrrolidinol,1-methyl-5-nonyl-2-(phenylmethyl)-, [2S-(2a,3a,5a)]-; (+)-Preussin; Preussin; Preussine

Chemical Property of 1-Methyl-2β-benzyl-5β-nonylpyrrolidine-3β-ol

Chemical Property:

• Vapor Pressure: 3.1E-08mmHg at 25°C
• Boiling Point: 432.1°Cat760mmHg
• Flash Point: 11.1°C
• PSA: 23.47000
• Density: 0.967g/cm³
• LogP: 4.74130

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• General Description: (+)-Preussin (1-Methyl-2β-benzyl-5β-nonylpyrrolidine-3β-ol) is a bioactive alkaloid characterized by a pyrrolidine core substituted with a benzyl group at the 2-position, a nonyl chain at the 5-position, and a hydroxyl group at the 3-position. It exhibits stereochemical complexity, with the described configuration ([2S-(2α,3α,5α)]) indicating its specific spatial arrangement. The compound has been synthesized efficiently via a one-pot reductive alkylation method, demonstrating its relevance as a target in alkaloid synthesis due to its structural features and potential bioactivity.

Technology Process of 1-Methyl-2β-benzyl-5β-nonylpyrrolidine-3β-ol

There total 207 articles about 1-Methyl-2β-benzyl-5β-nonylpyrrolidine-3β-ol 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: 100.0%

(2S,3S,5R)-2-(phenylmethyl)-1-carbomethoxy-5-nonyl-3-pyrrolidinol (131013-30-4) → (+)-preussin (125356-66-3,119463-16-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h; Heating;

DOI:10.1021/jo00003a040

Reference yield: 98.0%

(2S,3S,5S)-2-Benzyl-1-methyl-5-((E)-non-1-enyl)-pyrrolidin-3-ol → (+)-preussin (125356-66-3,119463-16-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; under 760 Torr;

DOI:10.1055/s-1997-1347

Reference yield: 94.0%

(2S,3S,5R)-3-Acetoxy-1-ethoxycarbonyl-2-benzyl-5-nonylpyrrolidine (159154-02-6) → (+)-preussin (125356-66-3,119463-16-0)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 2.5h; Heating;

DOI:10.1021/ja00104a005

upstream raw materials:

(2S,3S,5R)-2-(phenylmethyl)-1-carbomethoxy-5-nonyl-3-pyrrolidinol

tert-butyl (2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine-1-carboxylate

(S)-2-Benzyl-5-nonyl-3-oxo-2,3-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

(2S,3S,5R)-3-Acetoxy-1-ethoxycarbonyl-2-benzyl-5-nonylpyrrolidine

Refernces

Versatile one-pot reductive alkylation of lactams/amides via amide activation: Application to the concise syntheses of bioactive alkaloids (±)-bgugaine, (±)-coniine, (+)-preussin, and (-)-cassine

10.1002/chem.201002054

The research focuses on the development of a versatile one-pot reductive alkylation method for the transformation of lactams and amides into α-substituted amines, which are key structural features in many bioactive alkaloids and pharmaceutically relevant molecules. The study aimed to improve the efficiency of organic synthesis by utilizing a triflic anhydride (Tf2O)/2,6-di-tert-butyl-4-methylpyridine (DTBMP) combination as the amide activating system, Grignard reagents as alkylating agents, and lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4) as reducing agents. The methodology was demonstrated through the concise syntheses of bioactive alkaloids (-)-bgugaine, (-)-coniine, (+)-preussin, and (-)-cassine, showcasing the method's diastereoselectivity and versatility. The successful syntheses of these alkaloids not only highlight the efficiency of the developed method but also its potential for further application in the total synthesis of other alkaloids.