119463-16-0

Basic information

• Product Name: preussin
• Synonyms: preussin;1-Methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol;L-657398
• CAS NO: 119463-16-0
• Molecular Formula: C21H35NO
• Molecular Weight: 317.5087
• Mol File: 119463-16-0.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 432.1°Cat760mmHg
• Flash Point: 11.1°C
• Appearance: /
• Density: 0.967g/cm³
• Vapor Pressure: 3.1E-08mmHg at 25°C
• Refractive Index: 1.516
• PKA: 14.95±0.60(Predicted)
• CAS DataBase Reference: preussin(CAS DataBase Reference)
• NIST Chemistry Reference: preussin(119463-16-0)
• EPA Substance Registry System: preussin(119463-16-0)

Safety Data

• Hazardous Substances Data: 119463-16-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H35NO/c1-3-4-5-6-7-8-12-15-19-17-21(23)20(22(19)2)16-18-13-10-9-11-14-18/h9-11,13-14,19-21,23H,3-8,12,15-17H2,1-2H3

Upstream product

• 205491-16-3 (S)-tert-butyl (4-((tert-butyldiphenylsilyl)oxy)-1-hydroxybutan-2-yl)carbamate 
• 108-86-1 bromobenzene 
• 210964-91-3 (4R,5S)-5-benzyl-3,3-dichloro-4-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]-2-pyrrolidinone 
• 210964-89-9 (+)-(4S,5S)-5-benzyl-4-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]-2-pyrrolidinone 
• 223118-85-2 (2R,3S)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-4-(2-nonyl-[1,3]dioxolan-2-yl)-butyric acid 
• 196491-86-8 (2R,3S)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-4-(2-nonyl-[1,3]dioxolan-2-yl)-butyramide 
• 223117-48-4 methyl (3S)-3-[dimethyl(phenyl)silyl]-5-oxotetradecanoate 
• 196491-87-9 [(1S,2S)-1-Benzyl-2-(dimethyl-phenyl-silanyl)-4-oxo-tridecyl]-carbamic acid benzyl ester 
• 223118-05-6 (S)-4-Benzyl-3-[(S)-3-(dimethyl-phenyl-silanyl)-4-(2-nonyl-[1,3]dioxolan-2-yl)-butyryl]-oxazolidin-2-one 
• 196491-83-5 (S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-tetradecane-1,5-dione 
• 196491-85-7 (2R,3S)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-4-(2-nonyl-[1,3]dioxolan-2-yl)-butyric acid methyl ester 
• 196491-88-0 (2S,3S,5R)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-5-nonyl-pyrrolidine-1-carboxylic acid ethyl ester 
• 196491-84-6 (S)-3-(Dimethyl-phenyl-silanyl)-4-(2-nonyl-[1,3]dioxolan-2-yl)-butyric acid methyl ester 
• 39691-62-8 nonylmagnesium bromide 

Relevant articles and documents

Molecular Iodine-Mediated α-C-H Oxidation of Pyrrolidines to N,O-Acetals: Synthesis of (±)-Preussin by Late-Stage 2,5-Difunctionalizations of Pyrrolidine

We previously reported an iterative synthesis of unsymmetrical 2,5-disubstituted pyrrolidines from pyrrolidine by two rounds of redox-triggered α-C-H functionalization. Although this approach can be used to introduce substituents at the 2- and 5-positions, it is lengthy because the redox auxiliary must be removed and then reinstalled. Therefore, we sought to develop a method to oxidize 2-functionalized pyrrolidine to cyclic N,O-acetal which could then react with a nucleophile for introduction of the 5-substituent. In this work, we found that molecular iodine can mediate the preferential oxidation of secondary over tertiary α-C-H bonds of α-substituted pyrrolidines to form cyclic N,O-acetals, improving the step economy of our previously reported method. With this strategy, (±)-preussin and its C(3) epimer were synthesized from (±)-pyrrolidin-3-ol.

A concise and efficient synthesis of (+)-preussin

A novel and efficient synthesis of (+)-preussin (7) starting from N-butoxycarbonyl-L-phenylalaninal (1) is described. This natural product was synthesized under mild conditions and with good overall yield.

Asymmetric synthesis of 2,5-disubstituted 3-hydroxypyrrolidines based on stereodivergent intramolecular iridium-catalyzed allylic aminations

Intramolecular iridium-catalyzed allylic aminations of homochiral (E)-6-N-nosylaminohept-2-en-1-yl methyl carbonates were investigated. The relative position of the 2,5-substituents of the resulting pyrrolidines was found to be controlled by using both enantiomers (4 and 5) of the appropriate chiral ligand, demonstrating a simple and highly stereodivergent synthetic protocol. Selected trans- and cis-2,5-disubstituted 3-hydroxypyrrolidines (2a and 18a) were converted to (+)-bulgecinine (6) and (+)-preussin (7), respectively.