113794-42-6

Basic information

• Product Name: Butanoic acid, 1-(1-naphthalenyl)ethyl ester, (R)-
• CAS NO: 113794-42-6
• Molecular Formula: C16H18O2
• Molecular Weight: 242.318
• Mol File: 113794-42-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 1-(1-naphthalenyl)ethyl ester, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 1-(1-naphthalenyl)ethyl ester, (R)-(113794-42-6)
• EPA Substance Registry System: Butanoic acid, 1-(1-naphthalenyl)ethyl ester, (R)-(113794-42-6)

Safety Data

• Hazardous Substances Data: 113794-42-6(Hazardous Substances Data)

Upstream product

• 123-20-6 vinyl n-butyrate 
• 57605-95-5 1-(1-naphthyl)ethanol 
• 57392-44-6 2,2,2-trichloroethyl butyrate 

Downstream Products

• 42177-25-3 (R)-1-(naphth-1-yl)ethanol 

Relevant articles and documents

Lipase catalyzed kinetic resolution of (±)-1-(1-naphthyl) ethanol under microwave irradiation

1-(1-Naphthyl) ethanol is an important chiral building block for the synthesis of active pharmaceutical intermediates (APIs). In this work, lipase catalyzed kinetic resolution of (RS)-1-(1-naphthyl) ethanol via transesterification was studied under microwave irradiation with different acyl donors. Vinyl acetate was the most effective and hence used as the acyl donor. Three different commercially available immobilized lipases were used, among which Candida antarctica lipase B, immobilized on acrylic resin (Novozym 435) was found to be the best catalyst in n-heptane as solvent. The effect of various parameters was studied in a systematic manner. The reaction was intrinsically kinetically controlled. Maximum conversion of 47.74% with enantiometric excess of substrate (ees) of 90.05% and enantiomeric ratio (E) of 433.39 was obtained in 3 h using 30 mg of enzyme loading with equi-molar ratio of alcohol to ester at 60°C. From the progress curve analysis, the ping-pong bi-bi mechanism with inhibition by both substrates was found to fit the initial rates. Kinetic parameters were obtained by using non-linear regression. The process is efficient and easily scalable as compared to the chemical process.

Chemical-enzyme method used for synthesis of cinacalcet

The invention discloses a chemical-enzyme method used for synthesis of cinacalcet. The chemical-enzyme method cmprises following steps: under catalyst effect of lipase, racemic 1-(1-naphthyl)ethanol and a fatty acid vinyl ester are subjected to kinetic resolution in a solvent so as to obtain (S)-1-(1-naphthyl) ethanol; under the effect of a catalyst, (S)-1-(1-naphthyl) ethanol and 3-(3-(trifluoromethyl)phenyl)propylamine are subjected to Mitsunobu reaction so as to obtain cinacalcet. According to the chemical-enzyme method, racemic 1-(1-naphthyl)ethanol is taken as an initial raw material, biological enzyme resolution is adopted so as to obtain (S)-1-(1-naphthyl) ethanol, and (S)-1-(1-naphthyl) ethanol and 3-(3-(trifluoromethyl)phenyl)propylamine are subjected to Mitsunobu reaction so asto obtain cinacalcet. Compared with the prior art, the advantages are that: reaction steps are few; operation is simple; no high pressure container is used for hydrogenation reduction; no expensive reducing agent is used; reaction conditions are mild; safety is high; the yield and purity are high; and the purity is as high as 99% or higher.