76155-79-8 | (R)-1-[4-(TRIFLUOROMETHYL)PHENYL]ETHANOL

CAS:76155-79-8 | (R)-1-[4-(TRIFLUOROMETHYL)PHENYL]ETHANOL,Description

“(1R)-1-[4-(trifluoromethyl)phenyl]ethanol” is an important pharmaceutical intermediate. It is a key intermediate for the synthesis of aprepitant, a potent human neurokinin-1 (NK-1) receptor.

Synthesis Analysis

The synthesis of “(1R)-1-[4-(trifluoromethyl)phenyl]ethanol” can be achieved through the asymmetric reduction of 4-(trifluoromethyl)acetophenone. This process is performed by recombinant Escherichia coli cells with excellent enantioselectivity. To overcome the conversion limitation due to the poor solubility of the non-natural substrate, a polar organic solvent-aqueous medium was established to improve the efficacy. Isopropanol was selected as the most suitable cosolvent candidate. Under the optimum conditions, the preparative-scale asymmetric reduction generated a 99.1% yield with >99.9% product enantiomeric excess (ee) in a 15% (v/v) isopropanol proportion, at 100 mM of 4-(trifluoromethyl)acetophenone within 3 hours.

Molecular Structure Analysis

The molecular formula of “(1R)-1-[4-(trifluoromethyl)phenyl]ethanol” is C9H9F3O.

Chemical Reactions Analysis

The chemical reaction involved in the synthesis of “(1R)-1-[4-(trifluoromethyl)phenyl]ethanol” is the asymmetric reduction of 4-(trifluoromethyl)acetophenone. This reaction is catalyzed by recombinant Escherichia coli cells.

Scientific Research Applications

1. Biocatalytic Preparation

• Application Summary : “(1R)-1-[4-(trifluoromethyl)phenyl]ethanol” is an important pharmaceutical intermediate of a chemokine CCR5 antagonist. A bioprocess for the asymmetric reduction of 4-(trifluoromethyl)acetophenone to “(1R)-1-[4-(trifluoromethyl)phenyl]ethanol” was developed.
• Methods of Application : The process was carried out by recombinant Escherichia coli cells with excellent enantioselectivity. A polar organic solvent-aqueous medium was established to improve the efficacy. Isopropanol was selected as the most suitable cosolvent candidate.
• Results or Outcomes : Under optimum conditions, the preparative-scale asymmetric reduction generated a 99.1% yield with >99.9% product enantiomeric excess (ee) in a 15% (v/v) isopropanol proportion, at 100 mM of 4-(trifluoromethyl)acetophenone within 3 hours.

2. Fluorescence Imaging

• Application Summary : Functional fluorophores, including “(1R)-1-[4-(trifluoromethyl)phenyl]ethanol”, represent an emerging research field, distinguished by their diverse applications, especially in sensing and cellular imaging.
• Methods of Application : The specific methods of application for “(1R)-1-[4-(trifluoromethyl)phenyl]ethanol” in fluorescence imaging are not detailed in the source.
• Results or Outcomes : The outcomes of using “(1R)-1-[4-(trifluoromethyl)phenyl]ethanol” in fluorescence imaging are not detailed in the source.

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