114446-47-8

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-Chloro-1-phenyl-1-(2-methylphenoxy)propane is used as a chiral intermediate for the synthesis of Desmethyl atomoxetine, a compound with potential applications in the treatment of attention deficit hyperactivity disorder (ADHD) and other related conditions. Its role in the synthesis process is crucial for the development of effective medications that can help improve the quality of life for patients suffering from these disorders.
As a chiral intermediate, (R)-3-Chloro-1-phenyl-1-(2-methylphenoxy)propane plays a significant role in the production of enantiomerically pure compounds, which are essential in the pharmaceutical industry due to their potential for increased efficacy and reduced side effects compared to their racemic counterparts.

InChI:InChI=1/C16H17ClO/c1-13-7-5-6-10-15(13)18-16(11-12-17)14-8-3-2-4-9-14/h2-10,16H,11-12H2,1H3/t16-/m1/s1

Upstream product

• 100306-34-1 3-chloro-1-phenylpropanol 
• 95-48-7 ortho-cresol 
• 95-52-3 2-Fluorotoluene 
• 100306-33-0 (1R)-3-chloro-1-phenylpropanol 
• 71-43-2 benzene 
• 142037-19-2 Chloro-acetic acid (S)-3-chloro-1-phenyl-propyl ester 
• 141987-54-4 1-Phenyl-3-chlor-propyl-monochloracetat 
• 293322-40-4 3-Cloro-1-phenylpropyl butanoate 
• 18776-12-0 3-chloro-1-phenyl-propan-1-ol 
• 936-59-4 3-chloropropiophenone 

Downstream Products

• 105314-52-1 (R)-tomoxetine 
• 82248-59-7 atomoxetine hydrochloride 

Relevant academic research and scientific papers

Preparation method of cefamoxetine hydrochloride

The invention discloses a preparation method of tamoxidectin hydrochloride, belongs to the technical field of drug synthesis, and uses 3 - chlorine -1 - phenylpropanone as a raw material to undergo a reduction reaction. The synthesis route has the advantages of few reaction steps, mild reaction conditions,3 - simple 2 - operation, cheap -3 - and easily available raw materials, and low production cost 3 - and -1 - R-chloro - N - phenylpropanone is used as a raw material.

Candida tenuis xylose reductase catalyzed reduction of aryl ketones for enantioselective synthesis of active oxetine derivatives

Candida tenuis xylose reductase shows high catalytic efficiencies in carbonyl reduction of acetophenone and 1-phenyl-1-propanone derivatives. The quite low substrate solubility in aqueous buffer systems is circumvented by addition of methanol or by two-phase solvent systems. In the latter, methanol improves the substrate phase transfer as solvent mediator and leads to reasonable space/time yields. Resulting enantiomerically pure chiral alcohols are key intermediates for synthesis of active pharmaceutical ingredients. (R)-Atomoxetine is exemplarily synthesized in four steps, and the further use for generation of other oxetine derivatives and a polo-like kinase 1 inhibitor are discussed. Copyright

Asymmetric reduction of prochiral ketones using in situ generated oxazaborolidine derived from (1S,2S,3R,4R)-3-amino-7,7-dimethoxynorbornan-2-ol. An efficient synthesis of enantiopure (R)-tomoxetine

In this work, we report our results on the asymmetric reduction of prochiral aromatic and aliphatic ketones 3, 5-8 catalyzed by the novel in situ generated oxazaborolidine 2 derived from (1S,2S,3R,4R)-3-amino-7,7- dimethoxybornan-2-ol (1) and BH3?Me2S. This methodology was applied to the synthesis of the anti-depressant drug (R)-tomoxetine in three steps and 47% overall yield from 3-chloropropiophenone (3h). Catalytic asymmetric reduction of prochiral ketones was examined in the presence of chiral oxazaborolidine catalyst 2 prepared in situ from (1S,2S,3R,4R)-3-amino-7,7-dimethoxynorbornan-2-ol (1). The optically active secondary alcohols were generally obtained in moderate to high enantiomeric excesses (ee 43-95%) and good yields (75-94%), except for ketones bearing electron-withdrawing groups. The methodology was applied to the synthesis of enantiopure (R)-tomoxetine, a potent anti-depressant drug.

Chemoenzymatic synthesis of the non-tricyclic antidepressants Fluoxetine, Tomoxetine and Nisoxetine

3-Chloro-1-phenylpropan-1-ol and the corresponding butanoate, 3-chloro-1-phenyl-1-propyl butanoate, were kinetically resolved using lipase B from Candida antarctica catalysis by transesterification and hydrolysis respectively. The resulting chiral building blocks (S)- and (R)-3-chloro-1-phenylpropanol were converted into both enantiomers of the antidepressant drugs, Fluoxetine, Tomoxetine and Nisoxetine. The Royal Society of Chemistry 2000.

An efficient route to enantiomerically pure antidepressants: Tomoxetine, nisoxetine and fluoxetine

Both enantiomers (R)- and (S)-3-chloro-1-phenyl-1-propanol can be obtained conveniently by an efficient enzymatic resolution process. They can be converted via enantioconvergent routes into all enantiomers of the important antidepressants (R)- and (S)-Tomoxetine, Fluoxetine and Nisoxetine.

Iodinated tomoxetine derivatives as selective ligands for serotonin and norepinephrine uptake sites

In order to develop selective radioactive ligands for the study of presynaptic monoamine uptake sites, iodinated derivatives of tomoxetine were synthesized and evaluated in radioligand binding assays. Iodotomoxetine derivatives showed high affinity for serotonin (5-HT) uptake sites using a rat cortical membrane preparation. Compound 1R, (R)-(-)-N-methyl-3-(4-iodo-2- methyl]phenoxy)-3-phenylpropanamine, was the most potent and showed high stereoselectivity for 5-HT uptake sites (K(i), R isomer = 0.65 nM, S isomer = 13.9 nM). Changing the position of the methyl group or eliminating the methyl group at the phenoxy ring resulted in a loss of stereoselectivity. Substitution of the methyl group of tomoxetine with iodine gave the R and S isomers of N-methyl-3-(2-iodophenoxy)-3-phenylpropanamine 4R and 4S. These compounds displayed stereoselectivity for the norepinephrine (NE) (K(i) values = 0.24 and 9.35 nM for R and S isomers, respectively). The in vitro binding data suggest that 1R and 4R are potential radioiodinated ligands for pharmacological studies of 5-HT and NE uptake sites, respectively.

Novel process of producing phenyl or substituted phenylalkylamine pharmaceutical agents and novel chiral intermediates of high enantiomeric purity useful therein

A process for producing the optically pure (+)- or (-) isomer of a phenyl- or substituted- phenylalkanolamine compounds having pharmacologic activity without the need for resoltuion processes ad novel intermediates useful in the process including optically pure haloalcohols are provided.

Chiral Synthesis via Organoboranes. 18. Selective Reductions. 43. Diisopinocampheylchloroborane as an Excellent Chiral Reducing Reagent for the Synthesis of Halo Alcohols of High Enantiomeric Purity. A Highly Enantioselective Synthesis of Both Optical Isomers of Tomoxetine, Fluoxetine, a

Diisopinocampheylchloroborane, dIpc2BCl, reduces ring and chain sustituted haloaralkyl ketones to the corresponding halo alcohols in excellent enantiomeric excess.In certain cases these alcohols can be upgraded by simple methods to essentially 100percent ee.For instance, (+)- or (-)-3-chloro-1-phenyl-1-propanol is initially obtained in 97percent ee.Simple recrystallisation then furnishes the pure enantiomers.These chiral halo alcohols are highly versatile intermediates.They can be readily cyclized to oxiranes and 2-substituted tetrahydrofurans with retention of chirality.Utilizing this methodology, we have developed an efficient, highly enantioselective synthesis of both optical isomers of the antidepressant drugs, Tomoxetine, Fluoxetine, and Nisoxetine, from the common intermediates (+)-or (-)-3-chloro-1-phenyl-1-propanol.