127641-25-2

Usage

Uses

(1R,2S)-2-Pyrrolidino-1-phenyl-1-propanol, is a chiral building block used in asymmetric synthesis. It is also used as a novel heterodimer chiral amide base for enantioselective deprotonation of ketones.

InChI:InChI=1/C13H19NO/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/t11-,13-/m0/s1

Upstream product

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

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 
• 592551-69-4 (1R,2S)-1-phenyl-2-pyrrolidinylpropanamine 
• 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 
• 1403388-28-2 C₁₅H₂₀F₃NO₂Zn 

Relevant academic research and scientific papers

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.

NOVEL PROCESS FOR PREPARATION OF OPTICALLY PURE NOREPHEDRINE AND ITS DERIVATIVES

The present invention relates to a novel process for preparation of norephedrine and its derivatives. The present invention also relates to a process for separation of individual isomers of norephedrine and its derivatives using suitable chiral resoluting agents.

Chiral α-alkylation/arylation in 1-phenyl-2-(1-pyrrolidinyl)-1-propanol through Grignard reactions

Complete asymmetric induction has been achieved during Grignard alkylations/arylations resulting in (1S,2R)- and (1R,2R)-1-phenyl-1-alkyl/aryl-2-(1-pyrrolidinyl)-1-propanols which are isolated as hydrochlorides.

Dimethylzinc-mediated, enantioselective synthesis of propargylic amines

A one-pot, enantioselective synthesis of N-aryl propargylic amines, using alkynylation reagents obtained from dimethylzinc and terminal acetylenes in combination with various aldehydes and o-methoxyaniline as starting materials, has been developed. Enanti

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.