95840-73-6

Usage

Chiral derivative

Serotonin

Usage

Precursor in the synthesis of pharmaceuticals and agrochemicals

Known effects

Sedative and recreational

Abuse

Often abused as a psychoactive drug

Medical applications

Treatment of sleep disorders and neurological conditions

Regulation

Controlled by various government agencies

Classification

Controlled substance in some countries

Upstream product

• 46292-93-7 R-(+)-phenylsuccinic acid 
• 74-97-5 chlorobromomethane 
• 189885-64-1 2,2'-(1-phenylethane-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 1237786-72-9 (S)-hexa-1,5-dien-3-ylbenzene 
• 15463-92-0 (S)-(+)-dimethyl 2-phenylsuccinate 
• 635-51-8 2-phenylsuccinic acid 
• 4036-30-0 (S)-2-phenylsuccinic acid 
• 100-42-5 styrene 
• 97-93-8 triethylaluminum 
• 6836-98-2 3-phenyldihydrofuran-2-one 
• 7633-38-7 di-tert-butyl fumarate 
• 98-80-6 phenylboronic acid 
• 447462-44-4 (R)-4-oxo-2-(4-dibenzylaminophenyl)-butyric acid methyl ester 
• 447462-51-3 (R)-4-oxo-2-(4-pyrrolidin-1-yl-phenyl)-butyric acid methyl ester 

Downstream Products

• 637762-35-7 C₂₄H₂₂O₄ 
• 59349-74-5 (S)-N-benzyl-3-phenylpyrrolidine 
• 134920-62-0 (2S)-2-phenylbutane-1,4-diol-di-p-toluenesulfonate 
• 134920-91-5 (2R)-2-phenylbutane-1,4-diol-di-p-toluenesulfonate 
• 883901-37-9 (S)-3-(4-nitro-phenyl)-1-propyl-pyrrolidine 
• 883901-38-0 (S)-3-(4-amino-phenyl)-1-propyl-pyrrolidine 
• 883901-36-8 (S)-3-phenyl-1-propyl-pyrrolidine 
• 164653-83-2 methanesulfonic acid (S)-4-methanesulfonyloxy-3-phenyl-butyl ester 
• 61548-78-5 (S)-(1,4-dibromobutan-2-yl)benzene 

Relevant academic research and scientific papers

Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols

We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80-95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (?)-preclamol and a chiral 2,5-disubstituted tetrahydropyran.

Asymmetric hydrogenation of allylic alcohols using ir?N,P-Complexes

In this study, a series of γ,γ-disubstituted and β,γ-disubstituted allylic alcohols were prepared and successfully hydrogenated using suitable N,P-based Ir complexes. High yields and excellent enantioselectivities were obtained for most of the substrates studied. This investigation also revealed the effect of the acidity of the N,P?Ir-complexes on the acid-sensitive allylic alcohols. DFT ΔpKa calculations were used to explain the effect of the N,P-ligand on the acidity of the corresponding Ir-complex. The selectivity model of the reaction was used to accurately predict the absolute configuration of the hydrogenated alcohols.

Silver-Assisted, Iridium-Catalyzed Allylation of Bis[(pinacolato)boryl]methane Allows the Synthesis of Enantioenriched Homoallylic Organoboronic Esters

Described here is an enantioselective approach of making chiral, β-substituted homoallylic organoboronic esters. In the presence of LiOtBu and a catalytic amount of silver salt, commercial bis[(pinacolato)boryl]methane participated in the iridi

Catalytic enantioselective ethylalumination of terminal alkenes: Substrate effects and absolute configuration assignment

The chemo- and enantioselectivity of the reaction of alkenes with AlEt3 catalyzed by bis(1-neomenthylindenyl)zirconium dichloride has been studied. The reaction with linear alkenes in a chlorinated solvent (CH2Cl2) gives m

Preparation of chiral 3-arylpyrrolidines via the enantioselective 1,4-addition of arylboronic acids to fumaric esters catalyzed by Rh(I)/chiral diene complexes

A highly efficient rhodium-catalyzed protocol for the preparation of 2-arylsuccinic esters and 3-arylpyrrolidines of high optical purity has been achieved. In the presence of 1 mol % of a chiral diene/Rh(I) catalyst, asymmetric addition of various arylbor

PRACTICAL METHOD FOR REDUCING ESTERS OR LACTONES

Esters and lactones can be respectively reduced to alcohols and diols in the presence of the Group 8 (VIII) transition metal complex, base and hydrogen gas (H2). An extremely practical reduction method can be provided by preferable combinations of the Group 8 (VIII) transition metal complex, the base, a used amount of the base, a pressure of hydrogen gas and a reaction temperature. This method is used in place of hydride reduction and is a useful method by which design of highly active catalysts can be relatively easily made while a high productivity can be expected.

Catalytic hydrogenation of carboxamides and esters by well-defined Cp*Ru complexes bearing a protic amine ligand

A novel catalytic method for the straightforward hydrogenation of carboxamides and esters to primary alcohols has been developed. Chiral modification in the ligand sphere of the well-defined Cp*Ru catalyst molecule opens up a new possibility for the development of an enantioselective hydrogenation of racemic substrates via dynamic kinetic resolution.

Pd-catalyzed enantioselective allyl-allyl cross-coupling

The Pd-catalyzed cross-coupling of allylic carbonates and allylB(pin) is described. The regioselectivity of this reaction is sensitive to the bite angle of the ligand, with small-bite-angle ligands favoring the branched substitution product. This mode of

Highly site- and enantioselective Cu-catalyzed allylic alkylation reactions with easily accessible vinylaluminum reagents

An efficient method for catalytic asymmetric allylic alkylation (AAA) of allylic phosphates with vinylaluminum reagents is reported. The vinylmetal reagents are prepared by reaction of commercially available DIBAL-H and a terminal alkyne. The resulting vi

HETEROCYCLIC ARYLSULPHONES SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE SEROTONIN 5HT6 RECEPTOR

The invention relates to compounds of the formula (I) wherein the variables have meanings given in the claims and the description. The invention also relates to the use of a compound of the formula (I) or a pharmaceutically acceptable salt thereof for pre