Process for producing heterocyclic compound
AssigneeTakeda Pharmaceutical Company Limited
InventorsMasatoshi Yamada, Sayuri Hirano, Ryoji Tsuruoka, Mitsuhisa Yamano
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Abstract
The present invention provides a method of efficiently producing an optically active 6-(3-aminopiperidin-1-yl)-2,4-dioxo -1,2,3,4-tetrahydropyrimidine derivative. The optically active piperidine-3-carboxamide or a derivative thereof, which is obtained by subjecting 1,4,5,6-tetrahydropyridine -3-carboxamide or a derivative thereof to an asymmetric reduction in the presence of a catalyst, is used as an intermediate.
Claims4
A method of producing an optically active form of a compound represented by the formula:
- wherein
- R2′, R3′ and R4′ are independently a hydrogen atom, an optionally substituted hydrocarbon group, or an optionally substituted heterocyclic group;
- or
- R2′ and R3′ in combination, or R3′ and R4′ in combination optionally form a 5- to 8-membered ring together with the adjacent atoms;
- R7 and R8 are independently an optionally substituted hydrocarbon group, a hydrogen atom, or an optionally substituted heterocyclic group;
- and
- the carbon atom marked with * is an asymmetric carbon atom,
- or a salt thereof, which comprises reacting an optically active form of a compound represented by the formula:
- wherein each symbol is as defined above,
- or a salt thereof, with a compound represented by the formula:
- wherein
- L1 is a leaving group, and
- the other symbols are as defined above,
- or a salt thereof.
A method of producing an optically active form of a compound represented by the formula:
- wherein
- R2′, R3′ and R4′ are independently a hydrogen atom, an optionally substituted hydrocarbon group, or an optionally substituted heterocyclic group, or
- R2′ and R3′ in combination, or R3′ and R4′ in combination optionally form a 5- to 8-membered ring together with the adjacent atoms;
- R7 and R8 are independently an optionally substituted hydrocarbon group, a hydrogen atom, or an optionally substituted heterocyclic group;
- and
- the carbon atom marked with * is an asymmetric carbon atom,
- or a salt thereof, which comprises subjecting an optically active form of a compound represented by the formula:
- wherein each symbol is as defined above,
- or a salt thereof, to a rearrangement reaction.
A ruthenium complex represented by the formula:
- [Ru(OCORa′)2La′] (VIII′)
- wherein
- Ra′ is a trifluoromethyl group;
- and
- La′ is an optically active diphosphine ligand selected from
- (1) an optically active form consisting of a compound represented by the formula:
- or
- the formula:
- or
- a mixture thereof, and
- (2) an optically active form of a compound represented by the formula:
- wherein the bond marked with * is a chiral axis.
Dependencies are inferred from the claim text.