123620-80-4

Usage

Uses

Used in Pharmaceutical Synthesis:
(1S,2R)-1-PHENYL-2-(1-PYRROLIDINYL)PROPAN-1-OL is utilized as an intermediate in the synthesis of various pharmaceuticals and organic compounds. Its unique molecular structure and stereochemistry make it a valuable component in creating new drugs with specific therapeutic targets.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (1S,2R)-1-PHENYL-2-(1-PYRROLIDINYL)PROPAN-1-OL is used as a building block for designing and developing novel molecules with potential therapeutic applications. Its stereochemistry plays a crucial role in determining the efficacy and selectivity of the resulting compounds.
Used in Drug Development:
(1S,2R)-1-PHENYL-2-(1-PYRROLIDINYL)PROPAN-1-OL is employed in drug development for its pharmacological activity as an agonist at certain G protein-coupled receptors. This property allows it to modulate cellular signaling pathways and potentially treat various diseases by interacting with specific biological targets.
Used in Research and Development:
In research and development, (1S,2R)-1-PHENYL-2-(1-PYRROLIDINYL)PROPAN-1-OL serves as a model compound for studying the effects of stereochemistry on biological activity. Its unique structure provides insights into the relationship between molecular configuration and pharmacological properties, aiding in the discovery of new drugs with improved efficacy and selectivity.

InChI:InChI=1/C13H19NO.ClH/c1-11(14-9-5-6-10-14)13(15)12-7-3-2-4-8-12;/h2-4,7-8,11,13,15H,5-6,9-10H2,1H3;1H/t11-,13-;/m1./s1

Upstream product

• 628-21-7 1,4-Diiodobutane 
• 37577-28-9 (1S,2R)-(+)-norphedrine 
• 123-75-1 pyrrolidine 
• 4436-22-0 1-phenylpropylene oxide 
• 71-43-2 benzene 
• 210558-66-0 (1R,2S)-(+)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol hydrochloride 
• 1215194-08-3 (S)-(-)-1-phenyl-2-(1-pyrrolidinyl)-1-propanone 
• 173676-57-8 1-phenyl-2-(pyrrolidin-1-yl)propan-1-ol 
• 93-55-0 1-phenyl-propan-1-one 
• 19134-50-0 (SR)-(+/-)-1-phenyl-2-(1-pyrrolidinyl)-1-propanone 
• 110-52-1 1,4-dibromo-butane 
• 492-41-1 (1R,2S)-norephedrine 

Downstream Products

• 1239346-72-5 (2S,3R,7aR)-3-methyl-2-phenylhexahydropyrrolo[2.1-b]oxazole 
• 166031-45-4 Thioacetic acid S-((1R,2S)-1-phenyl-2-pyrrolidin-1-yl-propyl) ester 
• 1403388-28-2 C₁₅H₂₀F₃NO₂Zn 
• 209414-27-7 (2S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol 
• 1224847-71-5 (1R,2S)-1-phenyl-2-(pyrrolidin-1-yl)propyl (2S)-5-[(tert-butoxycarbonyl)amino]-2-(4,5-dihydroimidazo[1,5-a]quinolin-3-ylmethyl)pentanoate 
• 1224847-72-6 (1R,2S)-1-phenyl-2-(pyrrolidin-1-yl)propyl (2R)-5-[(tert-butoxycarbonyl)amino]-2-(4,5-dihydroimidazo[1,5-a]quinolin-3-ylmethyl)pentanoate 
• 1224849-26-6 (1R,2S)-1-phenyl-2-(pyrrolidin-1-yl)propyl (2S)-5-[(tert-butoxycarbonyl)amino]-2-[(7-methyl-4,5-dihydroimidazo[1,5-a]quinolin-3-yl)methyl]pentanoate 
• 592551-69-4 (1R,2S)-1-phenyl-2-pyrrolidinylpropanamine 

Relevant academic research and scientific papers

Chiral Co(II) and Mn(II) catalysts for the 1,3-dipolar cycloaddition reactions of azomethine ylides derived from arylidene imines of glycine

Anhydrous MnBr2 and CoCl2 in conjunction with chiral ephedrine ligands effect substantial asymmetric induction in cycloadducts derived from methyl acrylate and imines of glycine methyl ester. CoCl2 is most effective and gi

A new norephedrine-derived chiral base for epoxide rearrangement reactions

The conversion of (1R,2S)-norephedrine into a novel chiral diamine (83% yield, simple two step synthesis) and its use as a chiral base in two epoxide rearrangement reactions is reported. Rearrangement of a 4,5-disubstituted cyclohexene oxide and of a 4-aminosubstituted cyclopentene oxide generated allylic alcohols of >90% ee. These results represent the highest levels of enantioselectivity reported to date for such substrates.

Kinetic and computational studies of the composition and structure of activated complexes in the asymmetric deprotonation of cyclohexene oxide by a norephedrine-derived chiral lithium amide

Rational design of efficient chiral lithium amides for enantioselective deprotonations demands understanding of the origin of the selectivity. The mechanism of deprotonation of cyclohexene oxide 1 by lithium (1R,2S)-N-methyl-1-phenyl-2-pyrrolidinylpropanamide 3, which yields (S)-cyclohex-2-en-1-ol (S)-5 in 93% enantiomeric excess in tetrahydrofuran (THF), has been investigated. Kinetics have been used to show that the reaction is first order with respect to the reagents 1 and 3, respectively. NMR investigations of a 6Li and 15N labelled isotopologue of 3 have previously shown that 3 is mainly a dimer of the lithium amide monomer in THF in the initial state. On the basis of these results it is concluded that the rate-limiting activated complexes for the epoxide deprotonation are composed of two molecules of monomer of lithium amide 3 and one molecule of epoxide. Structures and energies of unsolvated and specific THF-solvated reagents and activated complexes have been calculated using PM3 and B3LYP/6-31+G(d). The results are currently being explored for the rational design of chiral lithium amides with improved stereoselectivities.

Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases

Using a chiral base from a norephedrine-derived diamine, the enantioselective rearrangement of a meso-cyclohexene oxide can be performed in 94% yield and with 94% enantioselectivity. The enantioselectivity is lower (86% ee) with the diastereoisomeric chiral base. In order to prepare the diastereoisomeric chiral base, a potentially useful way of converting norephedrine into norpseudoephedrine was developed.

Enantioselective Conjugate Addition of Catalytically Generated Zinc Homoenolate

We report herein an enantioselective conjugate addition reaction of a zinc homoenolate, catalytically generated via ring opening of a cyclopropanol, to an α,β-unsaturated ketone. The reaction is promoted by a zinc aminoalkoxide catalyst generated from Et2Zn and a chiral β-amino alcohol to afford 1,6-diketones, which undergo, upon heating, intramolecular aldol condensation to furnish highly substituted cyclopentene derivatives with good to high enantioselectivities. The reaction has proved applicable to various 1-substituted cyclopropanols as well as chalcones and related enones. The chiral amino alcohol has proved to enable ligand-accelerated catalysis of the homoenolate generation and its conjugate addition. Positive nonlinear effects and lower reactivity of a racemic catalyst have been observed, which can be attributed to a stable and inactive heterochiral zinc aminoalkoxide dimer.

Synthesis method of chiral compound

The invention belongs to the technical field of chemical synthesis, and relates to a synthetic method of a chiral compound, in particular to a synthetic method of (1R, 2S)-1-phenyl-2-(pyrrolidine-1-yl) propan-1-ol. According to an ingenious synthesis strategy, asymmetric reduction can be realized during carbonyl reduction, and a target compound can be directly obtained at high yield. The problem that a target compound cannot be obtained at high yield through asymmetric reduction in the prior art is solved. Moreover, the synthesis of a high-purity compound (A) can be realized by using cheap hydrochloric acid and zinc chloride; in addition, no isomer is wasted; and according to the method, the use of norephedrine controlled product is avoided; the raw materials are cheap and easy to obtain,so that the synthesis cost is reduced; moreover, the preparation method disclosed by the invention is easy for industrial large-scale production.

ANTICANCER COMPOUND PROCESS

The present invention relates to a process for preparing compound 1 that useful as an anticancer agent. In particular, the invention seeks to provide new methodology for preparing compound 1 and substituted derivatives thereof.

Method for preparing chiral (1R,2S)-1-phenyl-2-(1-pyrrolidyl)propane-1-alcohol

The invention provides a new method for simply and feasibly synthesizing (1R,2S)-1-phenyl-2-(1-pyrrolidyl)propane-1-alcohol through enzymatic catalysis. The method is easy to operate and mild in condition, an intermediate does not need to be separated, th

A (S)- N - methoxy - methyl -2 - (tetrahydro-pyrrolyl) propionamide and its preparation method and application

The invention discloses a (S)-N-methoxy-methyl-2-(pyrrolidine) propionamide shown as a formula (5). A preparation method is as follows: subjecting a starting material L-alanine to amino protection, reaction with N,O-dimethyl hydroxylamine hydrochloride, removal of amino protecting group, and alkylation; and subjecting the prepared compound shown as (5) to addition elimination and reduction to obtain an Efavirenz chiral ligand shown as the formula (7). The synthetic method of Efavirenz chiral ligand provided by the invention has the advantages of mild reaction conditions, simple operation, high yield and low production cost, and is suitable for industrialized production.

Preparation method of (1R,2S)-1-phenyl-2-(1-pyrrolidyl)-1-propanol

The invention discloses a preparation method of (1R,2S)-1-phenyl-2-(1-pyrrolidyl)-1-propanol. According to the preparation method, DL-1-phenyl-2-(1-pyrrolidyl)-1-acetone is taken as a starting material and subjected to resolution, racemization and reduction, and (1R,2S)-1-phenyl-2-(1-pyrrolidyl)-1-propanol is prepared. The yield of one-time resolution is higher than 35%, a resolving agent is easy to recover, and the recovery rate is higher than 90%; the racemization process is performed under the slightly alkaline condition, and the racemization yield is higher; the yield of (1R,2S)-1-phenyl-2-(1-pyrrolidyl)-1-propanol obtained through reduction is higher than 85%. The preparation method has the advantages of mild reaction conditions, stable process, high product optical purity, low cost, high production safety and the like.