Preparation of a saturated aldehyde

Abstract

The invention relates to a compound according to Formula (IX) and salts thereof, wherein R 1 , R 2 and R 5 are each independently selected from H and hydrocarbon moieties, which hydrocarbon moieties optionally comprise one or more heteroatoms, and which hydrocarbons optionally comprise substituents, or when the compound according to formula (IX) is a salt, R 1 and/or R 2 may be a cation, R 3 , and R 4 each independently selected from hydrocarbon moieties, which hydrocarbon moieties optionally comprise one or more heteroatoms, and which hydrocarbons optionally comprise substituents, and wherein any two of R 1 , R 2 , R 3 , R 4 and R 5 are optionally linked together to form a ring structure. The invention further relates to the preparation of such a compound and to the use of such a compound for preparing a pharmaceutical compound, an agrochemical compound, an intermediate for a pharmaceutical compound or an intermediate for an agrochemical compound.

1 . Method for preparing a compound of the Formula (IX) 
       
         
           
           
               
               
           
         
         and salts thereof, wherein the method comprises: 
         converting the α,β carbon-carbon unsaturation of an E-isomer, a Z-isomer or a mixture of an E-isomer and a Z-isomer of a compound according to Formula (I) 
       
       
         
           
           
               
               
           
         
         wherein 
         R 1  and R 2  are each independently selected from H and hydrocarbon moieties, which hydrocarbon moieties optionally comprise one or more heteroatoms, and which hydrocarbon moieties optionally comprise substituents, or when the compound according to formula (IX) is a salt. R 1  and/or R 2  may be a cation, 
         R 3  and R 4  each independently are selected from the group of C 1 -C 6  alkyl and R 5  is selected from H, C 1 -C 6  alkoxyls, tri(C 1 -C 6  alkyl)silyls, C 1 -C 6  alkyls, and wherein R 1  and R 2  are optionally linked together to form a ring structure. 
       
     
     
         2 . Method according to  claim 1 , wherein the compound according to Formula (I), is converted using a catalyst selected from the group of heterogeneous hydrogenation metal catalysts, enzymes, and homogeneous hydrogenation catalysts. 
     
     
         3 . Method according to  claim 2 , wherein a homogeneous hydrogenation catalyst is used, in particular a metal or metal ion complex, more in particular a complex selected from the group of rhodium complexes, ruthenium complexes, iridium complexes and platinum complexes. 
     
     
         4 . Method according to  claim 2 , wherein an enzyme is used selected from the group of oxidoreductases, in particular from the group of ene reductases. 
     
     
         5 . Method according to  claim 1 , wherein the conversion of the α,β carbon-carbon unsaturation of an E-isomer, a Z-isomer or a mixture of an E-isomer and a Z-isomer of a compound according to Formula (I) is carried out under isomerising conditions, said isomerising conditions preferably comprising the presence of a compound capable of participating in a Michael addition and a retro-Michael addition, more preferably in the presence of a compound selected from the group of thiols, including thioalkohols; halogens; secondary amines; and tertiary amines. 
     
     
         6 . Method according to  claim 1 , wherein the compound of Formula (IX) is formed enantioselectively with respect to the R-isomer or the S-isomer, preferably the R-isomer is prepared in excess over the S-isomer. 
     
     
         7 . Method according to  claim 1 , wherein R 1  is 3-methoxypropyl, R 2 , is methyl, R 3 , is methyl, R 4  is methyl and R 5  is H. 
     
     
         8 . Method for preparing a compound according to Formula (II) 
       
         
           
           
               
               
           
         
         wherein 
         R 1  and R 2  are each independently selected from H and hydrocarbon moieties, which hydrocarbon moieties optionally comprise one or more heteroatoms, and which hydrocarbon moieties optionally comprise substituents, or when the compound according to formula (IX) is a salt, R 1  and/or R 2  may be a cation, 
         R 3  and R 4  each independently are selected from the group of C 1 -C 6  alkyl and R 5  is selected from H, C 1 -C 6  alkoxyls, tri(C 1 -C 6  alkyl)silyls, C 1 -C 6  alkyls, and wherein R 1  and R 2  are optionally linked together to form a ring structure, and 
         wherein the method comprises reducing the aldehyde group of a compound according to Formula (IX). 
       
     
     
         9 . Method according to  claim 8 , wherein the compound of Formula (II) is formed enantioselectively with respect to the R-isomer or the S-isomer, preferably wherein the R-isomer is prepared in excess of the S-isomer. 
     
     
         10 . Method according to  claim 8 , wherein the preparation is carried out under conditions under which the compound according to Formula (IX) is racemizing. 
     
     
         11 . Method according to  claim 8 , wherein a hydrogenation catalyst is present, preferably the hydrogenation catalyst is an enzyme, preferably an Alcoholdehydrogenase (ADH), or a homogeneous catalyst. 
     
     
         12 . Method for preparing a compound according to Formula (X) 
       
         
           
           
               
               
           
         
         wherein 
         R 1  and R 2  are each independently selected from H and hydrocarbon moieties, which hydrocarbon moieties optionally comprise one or more heteroatoms, and which hydrocarbon moieties optionally comprise substituents, or when the compound according to formula (IX) is a salt, R 1  and/or R 2  may be a cation, 
         R 3  and R 4  each independently are selected from the group of C 1 -C 6  alkyl and R 5  is selected from H, C 1 -C 6  alkoxyls, tri(C 1 -C 6  alkyl)silyls, C 1 -C 6  alkyls, and wherein R 1  and R 2  are optionally linked together to form a ring structure; and 
         Hal is a halogen atom, 
         wherein the method comprises substituting the hydroxyl of a compound according to Formula (II), obtained in a method according to  claim 8 , by a halogen atom, preferably Cl. 
       
     
     
         13 . Use of a compound according to  claim 1 , as an intermediate compound for preparing a pharmaceutically active compound or an agrochemical. 
     
     
         14 . Use of a compound according to  claim 1 , as an intermediate compound for preparing a compound according to the Formula (XVII) or a suitable salt thereof, in particular a fumerate salt, 
       
         
           
           
               
               
           
         
         wherein 
         R 1  and R 2  are each independently selected from H and hydrocarbon moieties, which hydrocarbon moieties optionally comprise one or more heteroatoms, and which hydrocarbon moieties optionally comprise substituents, or when the compound according to formula (IX) is a salt, R 1  and/or R 2  may be a cation, 
         R 3  and R 4  each independently are selected from the group of C 1 -C 6  alkyl and R 5  is selected from H, C 1 -C 6  alkoxyls, tri(C 1 -C 6  alkyl)silyls, C 1 -C 6  alkyls, and wherein R 1  and R 2  are optionally linked together to form a ring structure.