6908-75-4

Basic information

• Product Name: Pyrrolidine, 1-(2-phenylethyl)-
• CAS NO: 6908-75-4
• Molecular Formula: C12H17N
• Molecular Weight: 175.274
• Mol File: 6908-75-4.mol

Chemical Properties

• CAS DataBase Reference: Pyrrolidine, 1-(2-phenylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolidine, 1-(2-phenylethyl)-(6908-75-4)
• EPA Substance Registry System: Pyrrolidine, 1-(2-phenylethyl)-(6908-75-4)

Safety Data

• Hazardous Substances Data: 6908-75-4(Hazardous Substances Data)

Upstream product

• 123-75-1 pyrrolidine 
• 103-63-9 1-phenyl-2-bromoethane 
• 1016-50-8 N-phenethylsuccinimide 
• 110-52-1 1,4-dibromo-butane 
• 64-04-0 phenethylamine 
• 110-63-4 Butane-1,4-diol 
• 73160-83-5 1-(1-methylsulfanyl-2-phenyl-ethylidene)-pyrrolidinium; iodide 
• 638-37-9 butanedial 
• 19213-23-1 1-((pyrrolidin-1-yl)methyl)-1H-benzo[d][1,2,3]triazole 
• 6921-34-2 benzylmagnesium chloride 
• 111290-73-4 1-Benzyl-1-trimethylsilanylmethyl-pyrrolidinium; iodide 
• 123-91-1 1,4-dioxane 
• 100-42-5 styrene 
• 60-12-8 2-phenylethanol 

Downstream Products

• 127236-89-9 1-Benzotriazol-1-ylmethyl-1-phenethyl-pyrrolidinium; iodide 
• 10220-22-1 1-(4-nitro-phenyl)-pyrrolidine 
• 65486-36-4 1-phenethyl-pyrrolidine-2-thione 

Relevant articles and documents

Insights into Rare-Earth Metal Complex-Mediated Hydroamination

Since the precise understanding of the underlying mechanism is important for the rational design of catalysts, much attention has been paid for hydroamination reactions catalyzed by organolanthanides during the past three decades. Distinct mechanisms were

A potassium magnesiate complex: Synthesis, structure and catalytic intermolecular hydroamination of styrenes

A new heterobimetallic potassium magnesiate complex KMg[N(SiMe3)2]2Bn (Bn = PhCH2-) was synthesized by simply mixing magnesium amide and potassium benzyl in toluene. The TMEDA-ligated potassium magnesiate comple

B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of: In situ -formed enamines

A highly efficient B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of in situ-formed enamines in the presence of water and pinacolborane was developed. Regioselective β-deuteration of tertiary amines was achieved with high chemo- and regioselectivity. D2O was used as a readily available and cheap source of deuterium. Mechanistic studies indicated that B(C6F5)3 could activate water to promote the protonation and reduction of enamines. This journal is

Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols

We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.

Atomic Pt-Catalyzed Heterogeneous Anti-Markovnikov C-N Formation: Pt10Activating N-H for Pt1δ+-Activated C-C Attack

C-N formation is of great significance to synthetic chemistry, as N-containing products are widely used in chemistry, medicine, and biology. Addition of an amine to an unsaturated carbon-carbon bond is a simple yet effective route to produce new C-N bonds. But how to effectively conduct an anti-Markovnikov addition with high selectivity has been a great challenge. Here, we proposed a strategy for highly regioselective C-N addition via hydroamination by using supported Pt. It has been identified that atomic-scale Pt is the active site for C-N addition with Pt12+ for Markovnikov C-N formation and atomic Pt (Pt1δ+ and Pt10) contributing to anti-Markovnikov C-N formation. A selectivity of up to 92% to the anti-Markovnikov product has been achieved with atomic Pt in the addition of styrene and pyrrolidine. A cooperating catalysis for the anti-Markovnikov C-N formation between Pt1δ+ and Pt10 has been revealed. The reaction mechanism has been studied by EPR spectra and in situ FT-IR spectra of adsorption/desorption of styrene and/or pyrrolidine. It has been demonstrated that Pt10 activates amine to be electrophilic, while Pt1δ+ activates C-C by π-bonding to make β-C nucleophilic. The attack of nucleophilic β-C to electrophilic amine affords the anti-Markovnikov addition. This strategy proves highly effective to a variety of substrates in anti-Markovnikov C-N formation, including aromatic/aliphatic amines reacting with aromatic olefins, aromatic/aliphatic olefins with aromatic amines, and linear aliphatic olefins with secondary aliphatic amines. It is believed that the results provide evidence for the function of varied chemical states in monatomic catalysis.

Ambient Moisture Accelerates Hydroamination Reactions of Vinylarenes with Alkali-Metal Amides under Air

A straightforward alkali-metal-mediated hydroamination of styrenes using biorenewable 2-methyltetrahydrofuran as a solvent is reported. Refuting the conventional wisdom of the incompatibility of organolithium reagents with air and moisture, shown here is that the presence of moisture is key in favoring formation of the target phenethylamines over competing olefin polymerization products. The method is also compatible with sodium amides, with the latter showing excellent promise as highly efficient catalysts under inert atmosphere conditions.

Photoinduced Cascade Reaction of Tertiary Amines with Sulfonyl Azides: Synthesis of Amidine Derivatives

A metal-free cascade reaction of tertiary amines with sulfonyl azides promoted by acridinium salts under blue light irradiation was developed and provided amidine derivatives in moderate to good yields. Enamine was generated from tertiary amine via single-electron transfer promoted by acridinium salts, and the following [3+2] cyclization with sulfonyl azide and CH2N2 release afforded the desired products. (Figure presented.).

Visible-Light-Mediated C(sp3)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide

We report herein a protocol for thiolactam preparation with potassium sulfide via visible-light-mediated C(sp3)–H thiocarbonylation, in which polysulfide dianions and radical anions generated from potassium sulfide were the key active species. A variety of thiolactams were straightforward established under mild conditions. Moreover, it was successfully applied to structural modification of tetrahydroberberine.

Alkali metal and stoichiometric effects in intermolecular hydroamination catalysed by lithium, sodium and potassium magnesiates

Main group bimetallic complexes, while being increasingly used in stoichiometric deprotonation and metal-halogen exchange reactions, have not yet made a significant impact in catalytic applications. This paper explores the ability of alkali metal magnesiates to catalyse the intermolecular hydroamination of alkynes and alkenes using sytrene and diphenylacetylene as principle setting model substrates. By systematically studying the role of the alkali-metal and the formulation of the heterobimetallic precatalyst, this study establishes higher order potassium magnesiate [(PMDETA)2K2Mg(CH2SiMe3)4] (7) as a highly effective system capable of catalysing hydroamination of styrene and diphenylacetylene with several amines while operating at room temperature. This high reactivity contrasts with the complete lack of catalytic ability of neutral Mg(CH2SiMe3)2, even when harsher reaction conditions are employed (24 h, 80 °C). A pronounced alkali metal effect is also uncovered proving that the alkali metal (Li, Na, or K) is not a mere spectating counterion. Through stoichiometric reactions, and structural and spectroscopic (DOSY NMR) investigations we shed some light on the potential reaction pathway as well as the constitution of key intermediates. This work suggests that the enhanced catalytic activity of 7 can be rationalised in terms of the superior nucleophilic power of the formally dianionic magnesiate {Mg(NR2)4}2- generated in situ during the hydroamination process, along with the ability of potassium to engage in π-interactions with the unsaturated organic substrate, enhancing its susceptibility towards a nucleophilic attack by the amide anion.

Chemoselective amide reductions by heteroleptic fluoroaryl boron Lewis acids

The heteroleptic borane catalyst (C6F5)2B(CH2CH2CH2)BPin is found to hydrosilylatively reduce amides under mild conditions. Simple tertiary amides can be reduced using Me2EtSiH, whereas tertiary benzamides required a more reactive secondary silane, Et2SiH2, for efficient reduction. The catalytic system described exhibits exceptional chemoselectivity in the reduction of oligoamides and tolerates functionalities which are prone to reduction under similar conditions.