118970-92-6

Basic information

• Product Name: (S)-2-(1-BENZYLPYRROLIDIN-2-YL)PROPAN-2-OL
• Synonyms: (S)-2-(1-BENZYLPYRROLIDIN-2-YL)PROPAN-2-OL
• CAS NO: 118970-92-6
• Molecular Formula: C₁₄H₂₁NO
• Molecular Weight: 219.326
• Mol File: 118970-92-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-2-(1-BENZYLPYRROLIDIN-2-YL)PROPAN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(1-BENZYLPYRROLIDIN-2-YL)PROPAN-2-OL(118970-92-6)
• EPA Substance Registry System: (S)-2-(1-BENZYLPYRROLIDIN-2-YL)PROPAN-2-OL(118970-92-6)

Safety Data

• Hazardous Substances Data: 118970-92-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-2-(1-BENZYLPYRROLIDIN-2-YL)PROPAN-2-OL is used as a key intermediate in the synthesis of various drugs, contributing to the development of novel pharmaceuticals with improved efficacy and safety profiles.
Used in Asymmetric Synthesis:
In the field of organic chemistry, (S)-2-(1-BENZYLPYRROLIDIN-2-YL)PROPAN-2-OL serves as a chiral auxiliary, playing a crucial role in asymmetric synthesis to produce enantiomerically pure compounds, which are essential for the pharmaceutical industry.
Used in the Treatment of Neurological Disorders:
(S)-2-(1-BENZYLPYRROLIDIN-2-YL)PROPAN-2-OL is being investigated for its potential therapeutic applications in the treatment of neurological disorders, given its unique structural features and biological activities.
Used in the Treatment of Mood Disorders:
(S)-2-(1-BENZYLPYRROLIDIN-2-YL)PROPAN-2-OL is also being explored for its potential use in the treatment of mood disorders, as it may offer new avenues for developing more effective therapies for patients suffering from such conditions.
Used in Chemical Research:
(S)-2-(1-BENZYLPYRROLIDIN-2-YL)PROPAN-2-OL is utilized in chemical research to study the effects of chirality on the properties and reactivity of molecules, which can lead to advancements in the design and synthesis of new compounds with specific applications.

Upstream product

• 147-85-3 L-proline 
• 676-58-4 methylmagnesium chloride 
• 113304-84-0 N-benzyl-(S)-proline methyl ester 
• 100-39-0 benzyl bromide 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 75-16-1 methylmagnesium bromide 
• 917-64-6 methyl magnesium iodide 
• 955-40-8 N-benzyl-L-proline ethyl ester 

Downstream Products

• 118971-00-9 (S)-(-)-2-(1-methoxy-1-methylethyl)-pyrrolidine 
• 41720-99-4 (S)-(-)-2-(1-methylethyl)-pyrrolidine 
• 118970-96-0 (S)-(-)-1-benzyl-2-(1-methoxy-1-methylethyl)-pyrrolidine 
• 92053-25-3 (S)-(-)-2-(1-hydroxy-1-methylethyl)-pyrrolidine 

Relevant articles and documents

Iminium Catalysis inside a Self-Assembled Supramolecular Capsule: Modulation of Enantiomeric Excess

The noncovalent combination of a supramolecular host with iminium organocatalysis is described. Due to cation–π interactions the reactive iminium species is held inside the host and reacts in this confined environment. The products formed differ up to 92 % ee from the control experiments without added host. A model rationalizing the observed difference is presented.

Asymmetric Henry reaction catalysed by L-proline derivatives in the presence of Cu(OAc)2: Isolation and characterization of an in situ formed Cu(II) complex

Synthesis of asymmetric β-nitroalcohols by the Henry reaction is one of the most exploited carbon-carbon bond-forming reactions owing to the versatility of both functional groups for synthetic manipulation by functional group interconversion. Here we repo

PYRAZINE COMPOUNDS AS PHOSPHODIESTERASE 10 INHIBITORS

Pyrazine compounds, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

Water-compatible iminium activation: Organocatalytic Michael reactions of carbon-centered nucleophiles with enals

(Chemical Equation Presented) A pool of water-compatible catalysts, namely the chiral prolinol-based catalysts 1, has been developed for highly enantioselective C-C bond-forming Michael reactions in water (see scheme). The synthesis of (S)-Rolipram, a type IV phosphodiesterase inhibitor, was also demonstrated.

Enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl)imines catalyzed by β-aminoalcohols with the prolinol skeleton

Several β-aminoalcohols with the prolinol framework are shown to be very efficient catalysts for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl)imines. The use of 0.5 equiv of the catalyst leads to the expected addition products in good yields and with ee up to 94% in a reaction time of only 4 h at room temperature. This ee is the highest value reported so far using 0.5 equiv of an aminoalcohol as a promoter. High enantioselectivities are obtained in the addition of dialkylzincs to both aromatic and aliphatic imines. The amount of the catalyst can be reduced to 0.25 equiv with a slight decrease in the ee. A very interesting effect of the addition rate and temperature on the enantioselectivity was also observed.

A new class of modular chiral ligands with fluxional groups

In ligand design for asymmetric catalysis, the usual norm is to derive the face shielding elements from a chiral source. New ligands in which the face shielding is determined by fluxional groups are introduced. Their design, modular synthesis, and experim

Synthesis of W-propionylated (S)-(-)-2-(pyrrolidin-2-yl)propan2-ol and its use as a chiral auxiliary and selectivity marker in asymmetric aldol reactions

The N-propionylated pyrrolidine derivative and chiral auxiliary, (S)-(-)-2-(pyrrolidin-2-yl)propan-2-ol, was synthesised and used in stereoselective aldol reactions with benzaldehyde. Differences in stereoselectivity were investigated as a function of temperature, solvent, chelating agent and the amount of the chelating agent used by monitoring the 1H NMR spectra of the aldol adducts that were obtained. Among the additives that were investigated, Cp2ZrCl2 induced higher syn-selectivity, while SnCl2 induced higher syn-selectivity respectively. TMSCl was found to induce high selectivity for one syn- and one anti-diastereomer. Varying the ligand sets on titanium additives was found to induce differences in selectivity, with (i-PrO)3TiCl exhibiting syn-selectivity and Cp2TiCl2 exhibiting anti-selectivity. Differences in reactivity and stereoselectivity were also found to depend upon the amount of Lewis acid that was added. Methods for removal of the auxiliary were also investigated. Acidic hydrolysis was used successfully to obtain the desired 3-hydroxy-2-methyl-3-phenylpropionic acids, but was found to give low yields and resulted in a large amount of epimerisation. Furthermore, the ethyl esters of these hydroxy acids are easy to separate into pure syn- and anti-diastereomers by LC. The Royal Society of Chemistry 2000.

Optically active 3-amino-2H-azirines as synthons for enantiomerically pure α,α-disubstituted α-amino acids: Synthesis of the α-methylphenylalanine synthons and some model peptides

The synthesis of a novel 2-benzyl-2-methyl-3-amino-2H-azirine derivative with a chiral amino group is described. Chromatographic separation of the diastereoisomer mixture yielded the pure diastereoisomers 9a and 9b which are the D- and L-2-methylphenylalanine ((α-Me)Phe) synthons, respectively. The reaction of 9a and 9b with thiobenzoic acid and with Z-leucine yielded the monothiodiamides 10a and 10b and the dipeptide derivatives 11a and 11b, respectively. Methanolysis of 11b yielded 12b. The absolute configuration of 10a was established by X-ray crystallography. The absolute configuration of (α-Me)Phe in 12b has been deduced from the known configuration of L-leucine.

LARGE SCALE PREPARATION OF VERSATILE CHIRAL AUXILIARIES DERIVED FROM (S)-PROLINE

The synthesis of a variety of enantiomerically pure chiral auxiliaries based on (S)-proline and bearing sterically demanding side chains at the pyrrolidine moiety, such as the secondary amines (S)-3,5 and 7 and the hydrazines (S)-6, is described on a molar scale.As key step, the Grignard or RLi addition to the N-benzylated proline ester (S)-1 is used.