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US 7,582,776 B2Granted
Process for preparing arylaminopropanols
AssigneeLANXESS Deutschland GmbH
InventorsMarkus Eckert, Claus Dreisbach, Boris Bosch, Andreas Stolle
Life of this patent
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Abstract
The invention relates to a process for preparing enantiomerically enriched aryl-aminopropanols and to their use and also to intermediates.
Claims8
A method for preparing a 3-hydroxy-3-(2-thienyl)propionamide compound of the formula:
- Ar—CH(OH)—CH2—CO—NR1R2
- wherein
- Ar represents 2-thiophenyl, which is optionally monosubstituted or polysubstituted by fluoro, nitro, hydroxyl, C1-12-alkyl, C1-12-haloalkyl, C5-14-aryl and C1-8-alkoxy;
- and
- R1 and R2 are each independently hydrogen, C1-20-alkyl, C4-14-aryl or C5-15-arylalkyl;
- said process comprising reducing the compound of the formula:
- Ar—CO—CH2—CO—NR1 R2
- wherein
- Ar, R1 and R2 are as defined above;
- in the presence of a catalyst constituted from a ruthenium-containing compound of the formula:
- [RuX2(arene)]2
- wherein
- X is chlorine, bromine or iodine;
- and
- arene is a coordinated compound having 6 to 12 ring carbon atoms, which may be further substituted by up to 6 radicals, each of which is independently selected from the group consisting of C1-8-alkyl, benzyl and phenyl;
- and a compound of the formula:
- wherein
- R7 and R8 are each independently C1-20 -alkyl, C4-15-aryl or C5-16-arylalkyl, or R7 and R8 together are a straight-chain or branched C3-12-alkylene radical;
- and
- R9 is C1 -C20-alkyl, C1-C20-fluoroalkyl or C4-C15-aryl.
17 more elements
A method for preparing a 3-hydroxy-3-(2-thienyl)propionamide compound of the formula:
- Ar—CH(OH)—CH2—CO—NR1R2
- wherein
- Ar represents 2-thiophenyl, which is optionally monosubstituted or polysubstituted by fluoro, nitro, hydroxyl, C1-12-alkyl, C1-12-haloalkyl, C5-14-aryl and C1-8-alkoxy;
- and
- R1 and R2 are each independently hydrogen, C1-20-alkyl, C4-14-aryl or C5-15-arylalkyl;
- said process comprising:
- a) reducing the compound of the formula:
- Ar—CO—CH2—CO—OR3
- wherein
- Ar is as defined above;
- and
- R3represents hydrogen, C1-20-alkyl, C4-14-aryl or C5-15-arylalkyl;
- in the presence of a catalyst constituted from a ruthenium-containing compound of the formula:
- [RuX2(arene)]2
- wherein
- X is chlorine, bromine or iodine;
- and
- arene is a coordinated compound having 6 to 12 ring carbon atoms, which may be further substituted by up to 6 radicals, each of which is independently selected from the group consisting of C1-8-alkyl, benzyl and phenyl;
- and a compound of the formula:
- wherein
- R7 and R8 are each independently C1-20-alkyl, C4-15-aryl or C5-16-arylalkyl, or R7 and R8 together are a straight-chain or branched C3-12-alkylene radical;
- and
- R9 is C1-C20-alkyl, C1-C20-fluoroalkyl or C4-C15-aryl;
- to form the resulting compound of the formula:
- Ar—CH(OH)—CH2—CO—OR3
- and then
- b)reacting said resulting compound with an amine of the formula:
- HNR1R2
- wherein
- R1 R2 have the meanings given above.
27 more elements
Dependencies are inferred from the claim text.