Process for production of optically active amine derivatives

Abstract

An industrial process for production of high-purity optically active amine derivatives in high yield while inhibiting the formation of by-products, which comprises subjecting (E)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)ethylamine to asymmetric reduction, catalytically reducing the obtained product at a reaction temperature of 40 to 100° C. and a pH of 3 to 9, subjecting the obtained (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine to propionylation, and then crystallizing the reaction mixture.

1 . A process for producing (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine or a salt thereof, which comprises step (i): a step for asymmetrically reducing (E)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)ethylamine or a salt thereof with a catalyst, and step (ii): a step for catalytically reducing the reaction product obtained in step (i) at a reaction temperature of 40° C. to 100° C. and pH 3 to 9 with a catalyst. 
     
     
         2 . The process according to  claim 1 , wherein the reaction temperature in step (ii) is 50° C. to 70° C. 
     
     
         3 . The process according to  claim 1 , wherein the pH in step (ii) is 5 to 7. 
     
     
         4 . The process according to  claim 1 , wherein the catalyst in step (i) is Ru-BINAP catalyst. 
     
     
         5 . The process according to  claim 1 , wherein the catalyst in step (ii) is Pd—C catalyst. 
     
     
         6 . A process for producing crystals of (S)—N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide, comprising step (a): a step for propionylating the amino group of (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine or a salt thereof obtained in the process according to  claim 1 , and step (b): a step for crystallizing by adding aqueous solvent to the reaction solution obtained in step (a). 
     
     
         7 . Crystals of (S)—N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide, wherein each content of the compounds represented by the following formulae (I), (II), (III) and (IV) is 0.15% by weight or less, and the total content of the compounds represented by the following formulae (I) to (IV) is 0.2% by weight or less. 
       
         
           
           
               
               
           
         
       
     
     
         8 . Crystals of (S)—N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide, wherein each content of the compounds represented by the following formulae (I), (III) and (IV) is 0.15% by weight or less, and the content of the compound represented by the following formula (II) is 0.02 to 0.15% by weight, and further the total content of the compounds represented by the following formulae (I) to (IV) is 0.2% by weight or less. 
       
         
           
           
               
               
           
         
       
     
     
         9 . The crystals according to  claim 7  or  8 , wherein the content of the compound represented by formula (I) is 0.10% by weight or less. 
     
     
         10 . A composition comprising (S)—N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide and the compounds represented by the following formulae (I), (II), (III) and (IV), wherein relative to 100 parts by weight of (S)—N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide, each content of the compounds represented by the following formulae (I), (II), (III) and (IV) is 0 to 0.15 part by weight and the total content of the compounds represented by the following formulae (I) to (IV) is 0 to 0.2 part by weight. 
       
         
           
           
               
               
           
         
       
     
     
         11 . A composition comprising (S)—N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide and the compounds represented by the following formulae (I), (II), (III) and (IV), wherein relative to 100 parts by weight of (S)—N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide, each content of the compounds represented by the following formulae (I), (III) and (IV) is 0 to 0.15 part by weight, and the content of the compound represented by the following formula (II) is 0.02 to 0.15 part by weight, and further the total content of the compounds represented by the following formulae (I) to (IV) is 0 to 0.2 part by weight. 
       
         
           
           
               
               
           
         
       
     
     
         12 . The composition according to  claim 10  or  11 , wherein the content of the compound represented by formula (I) is 0 to 0.10 part by weight relative to 100 parts by weight of (S)—N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide. 
       
         
           
           
               
               
           
         
       
     
     
         13 . The crystals according to  claim 7  or the composition according to  claim 10 , which is prepared on a commercial scale. 
     
     
         14 . A process for producing 1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one, comprising a step for reducing 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one with Pd—C catalyst under the condition:
   hydrogen pressure(MPa)>−0.02×gas-liquid overall mass transfer volume coefficient(1/hr)+0.43.
 
 
     
     
         15 . Use of the crystals according to  claim 7  for the manufacture of a preventive or therapeutic agent for sleep disorder. 
     
     
         16 . The composition according to  claim 10  which is a preventive or therapeutic agent for sleep disorder. 
     
     
         17 . A method for the prevention or treatment of sleep disorder, comprising administering the crystals according to  claim 8  or the composition according to  claim 10 .