1017158-54-1

Basic information

• Product Name: C₁₁H₁₃FO₃
• Synonyms: C₁₁H₁₃FO₃
• CAS NO: 1017158-54-1
• Molecular Weight: 212.221
• Mol File: 1017158-54-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: C₁₁H₁₃FO₃(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₁H₁₃FO₃(1017158-54-1)
• EPA Substance Registry System: C₁₁H₁₃FO₃(1017158-54-1)

Safety Data

• Hazardous Substances Data: 1017158-54-1(Hazardous Substances Data)

Upstream product

• 149437-76-3 5-(4-fluorophenyl)-5-oxopentanoic acid 
• 462-06-6 fluorobenzene 
• 108-55-4 glutaric anhydride, 

Downstream Products

• 1260675-05-5 6-(4-fluorophenyl)tetrahydro-2H-pyran-2-one 
• 1478664-18-4 (3S,4R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one 
• 1376614-99-1 (3S,4R)-1-(4-fluorophenyl)-3-((R)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one 
• 163222-33-1 ezetemibe 
• 163380-16-3 (3R,4S)-1-(4-fluorophenyl)-3-[(3R)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-azetidin-2-one 

Relevant articles and documents

Study on the HPLC-based separation of some ezetimibe stereoisomers and the underlying stereorecognition process

The enantioseparation of ezetimibe stereoisomers by high-performance liquid chromatography on different chiral stationary phases, ie, 3 polysaccharide-based chiral columns, was studied. It was observed that cellulose-based Chiralpak IC column exhibited the best resolving ability. After the optimization of mobile phase compositions in both normal and reversed phase modes, satisfactory separation could be obtained on Chiralpak IC column, especially in normal phase mode. The use of prohibited solvents as nonstandard mobile phase gave rise to better resolution than that of standard mobile phases (n-hexane/alcohol system). In addition, the presence of ethanol in nonstandard mobile phase has played an important role in enhancing chromatographic efficiency and resolution between ezetimibe stereoisomers. Various attempts were made to comprehensively compare the chiral recognition capabilities of immobilized versus coated polysaccharide-based chiral columns, amylose-based versus cellulose-based chiral stationary phases, reversed versus normal phase modes, and standard versus nonstandard mobile phases. Moreover, possible solute-mobile phase-stationary phase interactions were derived to explain how stationary and mobile phases affected the separation. Then the method validation with respect to selectivity, linearity, precision, accuracy, and robustness was carried out, which was demonstrated to be suitable and accurate for the quantitative determination of (RRS)-ezetimibe impurity in ezetimibe bulk drug.

Synthesis method of chiral methyl 5-(4-fluorophenyl)-5-hydroxyvalerate

The invention provides a synthesis method of chiral methyl 5-(4-fluorophenyl)-5-hydroxyvalerate. The method comprises the following steps: fluorobenzene and glutaric anhydride taken as raw materials undergo a Friedel-Crafts acylation reaction to synthesize 5-(4-fluorophenyl)-5-carbonylvaleric acid; the 5-(4-fluorophenyl)-5-carbonylvaleric acid undergoes a reduction reaction to synthesize 5-(4-fluorophenyl)-5-hydroxyvaleric acid; the 5-(4-fluorophenyl)-5-hydroxyvaleric acid undergoes a cyclization reaction to produce 6-(4-fluorophenyl)-tetrahydropyran-2-one; and the 6-(4-fluorophenyl)-tetrahydropyran-2-one undergoes an alcoholysis reaction to obtain the target compound, namely chiral methyl 5-(4-fluorophenyl)-5-hydroxyvalerate. The synthesis method avoids the problem that carbonyl and ester groups are easy to reduce at the same time, has the advantages of solution control of reaction conditions, high yield, mild reaction temperature, simplicity, easiness in implementation and low cost,and can realize industrial production.