127852-28-2Relevant articles and documents
Asymmetric Hydrogenation of 3,5-Bistrifluoromethyl Acetophenone in Pilot Scale with Industrially Viable Ru/Diphosphine-Benzimidazole Complexes
Xu, Liang,Huang, Zhi-Hong,Sandoval, Christian A.,Gu, Lian-Quan,Huang, Zhi-Shu
, p. 1137 - 1141 (2014)
A novel efficient asymmetric hydrogenation (AH) process was developed for the preparation of (R)-1-(3,5-bis(trifluoromethyl)phenyl)ethanol (3), using a catalyst Ru/(4R,5R)-(+)-4,5-bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxoane-(R,R-Diop)-2R-(α-met
A convergent approach to the synthesis of aprepitant: a potent human NK-1 receptor antagonist
Elati, Chandrashekar R.,Kolla, Naveenkumar,Gangula, Srinivas,Naredla, Anitha,Vankawala, Pravinchandra J.,Avinigiri, Muttu L.,Chalamala, Subrahmanyeswararao,Sundaram, Venkatraman,Mathad, Vijayavitthal T.,Bhattacharya, Apurba,Bandichhor, Rakeshwar
, p. 8001 - 8004 (2007)
A simple and convergent approach to enantiomerically pure 5-[[2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy-3-(4-fluorophenyl)morpholin-4-yl]methyl]-1,2-dihydro-1,2,4-triazol-3-one 1, a potent orally active antagonist of the human neurokinin-1 (NK-1) receptor, is described. The synthetic procedure starts from p-fluorobenzaldehyde to access the racemic morpholinone 2 via a modified Strecker synthesis and utilizes a diastereomeric salt resolution technique to accomplish the synthesis of 1 in enantiomerically pure form and good yield.
Efficient synthesis of (1R)-[3,5-bis(trifluoromethyl)phenyl] ethanol, a key intermediate for aprepitant, an NK-1 receptor antagonist
Vankawala, Pravinchandra J.,Kolla, Naveenkumar,Elati, Chandrashekar R.,Sreenivasulu,Kumar, K. Arun,Anjaneyulu, Yerrimilli,Venkatraman, Sundaram,Bhattacharya, Apurba,Mathad, Vijayavitthal T.
, p. 3439 - 3446 (2007)
Enzyme-catalyzed efficient synthesis of (1R)-[3,5-bis (trifluoromethyl) phenyl] ethanol (R)-(3), a key intermediate for aprepitant, via enantioselective transesterification of racemic 1-[3,5-bis (trifluoromethyl) phenyl] ethanol (RS)-3 using vinyl acetate as the acyl donor in the presence of Candida antarctica lipase-B (CAL-B) in an overall yield of 84% with >99% ee is described. Copyright Taylor & Francis Group, LLC.
Total production of (R)-3,5-bistrifluoromethylphenyl ethanol by asymmetric reduction of 3,5-bis(trifluoromethyl)-acetophenone in the submerged culture of Penicillium expansum isolate
Kurbanoglu, Esabi B.,Zilbeyaz, Kani,Taskin, Mesut,Kurbanoglu, Namudar I.
, p. 2759 - 2763 (2009)
A total of 82 fungal isolates were screened for their ability to reduce 3,5-bis(trifluoromethyl)-acetophenone 1. Penicillium expansum was found to successfully reduce ketone 1 in the submerged culture. A second screening was performed on the active P. exp
Bioreduction of 3,5-bis(trifluoromethyl)acetophenone using ionic liquid as a co-solvent catalyzed by recombinant Escherichia coli cells
Wang, Nengqiang,Li, Jun,Sun, Jing,Huang, Jin,Wang, Pu
, p. 119 - 125 (2015)
We investigated the asymmetric bioreduction of 3,5-bis(trifluoromethyl) acetophenone (BTAP) to (R)-[3,5-bis(trifluoromethyl) phenyl] ethanol ((R)-BTPE) in a hydrophilic quaternary ammonium-based ionic liquid (IL)-containing system to improve the efficiency of bioreduction catalyzed by recombinant Escherichia coli cells overexpressing carbonyl reductase. Based on the low toxicity to microbial cells and moderately increased cell membrane permeability, tetramethylammonium cysteine ([N1,1,1,1][Cys]) was selected and employed as co-solvent. Some key reaction parameters involved in the bioreduction were also investigated in the [N1,1,1,1][Cys]-containing system. The optimum conditions for the process were found to be: 3.5% (w/v) [N1,1,1,1][Cys], 20% (v/v) isopropanol, 1. M BTAP, 12.7. g/L of recombinant E. coli cells, pH 6.8, reaction for 12. h at 30. °C. A 98.7% yield (with >99 % of enantiomeric excess (ee)) was obtained under the optimum conditions. The biocatalytic process was scaled up to a 5. L fermentor afforded high reaction yield in IL-containing system. The results demonstrated that the IL [N1,1,1,1][Cys] is a useful co-solvent to improve bioreduction process and may has potential applications in various biocatalytic reactions.
Microbial and homogenous asymmetric catalysis in the reduction of 1-[3,5-bis(trifluoromethyl)phenyl]ethanone
Gelo-Pujic, Mirjana,Le Guyader, Frederic,Schlama, Thierry
, p. 2000 - 2005 (2006)
Two complementary approaches for the enantioselective reduction of 1-[3,5-bis(trifluoromethyl)phenyl]ethanone 1 are described and compared: microbial versus asymmetric reduction of ketones through asymmetric hydrogen transfer. Among the various microorgan
Identification of ketone reductase ChKRED20 from the genome of Chryseobacterium sp. CA49 for highly efficient anti-Prelog reduction of 3,5-bis(trifluoromethyl)acetophenone
Liu, Yan,Tang, Tuo-Xian,Pei, Xiao-Qiong,Zhang, Chao,Wu, Zhong-Liu
, p. 1 - 8 (2014)
A strain of Chryseobacterium sp. CA49 was isolated to perform efficient anti-Prelog reduction of 3,5-bis(trifluoromethyl)acetophenone (1a) to enantiopure (R)-3,5-bis(trifluoromethyl)-1-phenylethanol ((R)-1b), a key intermediate for the chiral drug Aprepit
Scalable, efficient process for the synthesis of (R)-3,5- bistrifluoromethylphenyl ethanol via catalytic asymmetric transfer hydrogenation and isolation as a DABCO inclusion complex
Hansen, Karl B.,Chilenski, Jennifer R.,Desmond, Richard,Devine, Paul N.,Grabowski, Edward J. J.,Heid, Richard,Kubryk, Michele,Mathre, David J.,Varsolona, Richard
, p. 3581 - 3587 (2003)
(R)-3,5-Bistrifluoromethylphenyl ethanol 2, a key building block in the synthesis of aprepitant, has been synthesized from ketone 5 via catalytic asymmetric transfer hydrogenation using a simplified catalyst generation procedure. The process uses (1S,2R)-
Effective synthesis of (S)-3,5-bistrifluoromethylphenyl ethanol by asymmetric enzymatic reduction
Pollard, David,Truppo, Matthew,Pollard, Jennifer,Chen, Cheng-yi,Moore, Jeffrey
, p. 554 - 559 (2006)
The synthesis of (S)-3,5-bistrifluoromethylphenyl ethanol, a pharmaceutically important alcohol intermediate for the synthesis of NK-1 receptor antagonists, was demonstrated from a ketone via asymmetric enzymatic reduction. The isolated enzyme alcohol dehydrogenase from Rhodococcus erythropolis reduced the poorly water soluble substrate with excellent ee (>99.9%) and good conversion (>98%). The optimized process was demonstrated up to pilot scale using high substrate concentration (390 mM) using a straightforward isolation process achieving excellent isolation yields (>90%) and effective space time yield (100-110 g/L d). Process improvements, demonstrated at preparative scale, increased the substrate concentration to 580 mM achieving a space time yield of 260 g/L d.
P/S ligands derived from carbohydrates in Rh-catalyzed hydrosilylation of ketones
Khiar, Noureddine,Leal, Manuel Pernia,Navas, Raquel,Moya, Juan Francisco,Perez, Maria Victoria Garcia,Fernandez, Inmaculada
, p. 355 - 360 (2012)
Reported is the synthesis of a number of diastereomerically pure cationic Rh(i)-complexes I starting from phosphinite thioglycosides. These complexes were used in the asymmetric hydrosilylation of prochiral ketones. The reactivity and enantioselectivity o
