89874-51-1

Upstream product

• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 96721-76-5 S-(-)-N-propyl-2-chloromethylpyrrolidine hydrochloride 
• 802294-64-0 propionic acid 
• 88784-37-6 (+)-(S)-3-(3-methoxyphenyl)piperidine 
• 85966-89-8 preclamol 
• 77-78-1 dimethyl sulfate 
• 4373-67-5 3-(3-methoxyphenyl)pyridine 
• 107-08-4 1-iodo-propane 
• 107-10-8 propylamine 
• 626-20-0 3-methoxystyrene 
• 3105-95-1 pipecolinic acid 
• 596121-81-2 dibenzyl 2-bromopentanedioate 
• 181705-90-8 (3-methoxyphenyl)zinc(II) bromide 
• 2398-37-0 3-methoxyphenyl bromide 

Downstream Products

• 147161-63-5 (S)-N-propyl-3-(3-methoxy-4-nitrophenyl)piperidine 
• 147161-65-7 (S)-N-propyl-3-(3-methoxy-4-aminophenyl)piperidine 
• 85966-89-8 preclamol 
• 85976-54-1 (+)-preclamol 
• 146798-88-1 S-(-)-3-<(3-(((trifluoromethyl)sulfonyl)oxy)phenyl)-N-n-propyl>piperidine 
• 1071930-35-2 trifluoromethanesulfonic acid 3-((S)-1-propyl-1-oxo-piperidin-3-yl)-phenyl ester 
• 89874-80-6 (+)-3-PPP hydrochloride 

Relevant academic research and scientific papers

Method for asymmetrically synthesizing (S)-preclamol

The invention discloses a novel method for asymmetrically synthesizing (S)-preclamol. The method comprises the following steps: using racemic alpha-halogenated glutaric acid diester as a starting material to be subjected to an asymmetric Negishi cross-coupling reaction with zinc m-methoxyphenyl bromide under the catalysis of a bisoxazoline chiral ligand and metal cobalt to obtain m-methoxyphenyl-substituted glutaric acid diester, then reducing by LiAlH4 to form (S)-2-(3-methoxyphenyl) pentanediol, and finally performing to amination cyclization and desmethylation to obtain (S)-preclamol. The asymmetric Negishi cross-coupling reaction is utilized for the first time to directly construct the chiral center of (S)-preclamol, the synthesis route is short, the reaction conditions are mild, and the total yield is 51%.

A Concise Enantioselective Synthesis of (S)-Preclamol via Asymmetric Catalytic Negishi Cross-Coupling Reaction

A novel, concise, and efficient enantioselective synthesis of (S)-preclamol (87% ee, 51% total yield) has been developed. The key steps of this synthetic approach included cobalt-catalyzed asymmetric catalytic cross-coupling of α-bromo ester with arylzinc and the reduction of chiral ester to diol with a tertiary carbon atom. Moreover, it was demonstrated that our enantioselective Negishi cross-coupling was a powerful tool to construct stereogenic benzylmethyl center in chiral drugs on a gram scale.

Stereoselective synthesis of (?)-3-PPP through palladium-catalysed unactivated C(sp3)–H arylation at the C-3 position of L-pipecolinic acid

An efficient route for the preparation of (?)-3-PPP(preclamol) using the highly stereoselective palladium-catalysed C(sp3)-H arylation and radical decarboxylation reaction as the key steps is described. The chiral center at the C-3 position of

A Cu/Pd Cooperative Catalysis for Enantioselective Allylboration of Alkenes

A cooperative Cu/Pd-catalyzed asymmetric three-component reaction of styrenes, B2(pin)2, and allyl carbonates was reported. This reaction, in the presence of chiral CuOAc/SOP and achiral Pd(dppf)Cl2 catalysts, occurs smoothly with high enantioselectivities (up to 97% ee). The allylboration products, which contain alkene (or diene) unite and alkylboron group, are easily functionalized. The utility of this protocol was demonstrated through the synthesis of an antipsychotic drug, ()-preclamol.

N-OXIDE AND/OR DI-N-OXIDE DERIVATIVES OF DOPAMINE RECEPTOR STABILIZERS/MODULATORS DISPLAYING IMPROVED CARDIOVASCULAR SIDE-EFFECTS PROFILES

The invention relates to N-oxide and/or di-N-oxide derivatives of dopamine receptor stabilizers/modulators having the general formula (1) or (2) and pharmaceutical preparations containing the said compounds. Further, the invention relates the use of the s

Dynamic kinetic resolution of racemic γ-aryl-δ-oxoesters. Enantioselective synthesis of 3-arylpiperidines

Cyclodehydration of racemic γ-aryl-δ-oxoesters with (R)- or (S)-phenylglycinol stereoselectively affords bicyclic δ-lactams, in a process that involves a dynamic kinetic resolution. Subsequent reduction of these lactams leads to enantiopure 3-arylpiperidines. Starting from racemic aldehyde esters, this short sequence has been applied to the synthesis of (R)-3-phenylpiperidine and the antipsychotic drug (-)-3-PPP (an (S)-3-arylpiperidine), whereas starting from racemic ketone esters enantiopure cis-2-alkyl-3-arylpiperidines are prepared.

Substituted (S)-phenylpiperidines and rigid congeners as preferential dopamine autoreceptor antagonists: Synthesis and structure-activity relationships

A series of (S)-phenylpiperidines in which the substituents on the aromatic ring and nitrogen have been varied has been prepared. They have been evaluated pharmacologically to explore the importance of these substituents for the interaction with central d

CHIRAL, POTENTIALLY IRREVERSIBLE LIGANDS FOR THE SIGMA RECEPTOR BASED ON THE STRUCTURE OF 3-(3-HYDROXYPHENYL)-N-PROPYLPIPERIDINE (3-PPP)

(+)-3-PPP is an optically active, highly potent and selective ligand for sigma receptors.The resolved enantiomeric pairs of potential irreversible sigma ligands (5a,b) and (9a,b) were designed and synthesized based on the structure of 3-PPP.An improved me

Resolved 3-(3-Hydroxyphenyl)-N-n-propylpiperidine and Its Analogues: Central Dopamine Receptor Activity

Seven enantiomeric pairs of N-alkyl analogues of 3-(3-hydroxyphenyl)-N-n-propylpiperidine (3-PPP, 12) have been synthesized and evaluated pharmacologically (biochemistry and behavior) in order to examine their ability to interact with central dopamine (DA