Method for manufacturing cyclopropane compound
AssigneeSumitomo Chemical Company, Limited
InventorsKazuhiro Yamauchi, Junichi Tomokawa
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Abstract
The present invention provides an industrially advantageous production method of (1R,2S)-2-{[((2,4-dimethylpyrimidin-5-yl)oxy}methyl]-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide. (1R,2S)-2-{[((2,4-Dimethylpyrimidin-5-yl)oxy}methyl]-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide (compound [A]) is produced by an industrially advantageous method by a route via a novel compound. wherein each symbol is as described in the description.
Claims6
A method of selectively producing an optically active compound represented by the formula [2]
- wherein R1 is an alkylcarbonyl group, and R2 is an alkyl group,
- the method comprising:
- reacting a compound represented by the formula [1]
- wherein R1 is an alkylcarbonyl group,
- with an alkyl diazoacetate in the presence of copper trifluoromethanesulfonate and an optically active compound represented by the formula [5] or formula [6]
- wherein tBu is a tert-butyl group,
- in an organic solvent.
A method of producing an optically active compound represented by the formula [4]
- the method comprising:
- reacting a compound represented by the formula [1]
- wherein R1 is an alkylcarbonyl group,
- with an alkyl diazoacetate in the presence of copper trifluoromethanesulfonate and an optically active compound represented by the formula [5] or formula [6]
- wherein tBu is a tert-butyl group,
- in an organic solvent to produce a mixture comprising an optically active compound represented by the formula [2]
- wherein R2 is an alkyl group, and R1 is an alkylcarbonyl group,
- and an optically active compound represented by the formula [2a]
- wherein R1 is an alkylcarbonyl group and R2 is an alkyl group;
- subjecting the mixture comprising the optically active compound represented by the formula [2] and the optically active compound represented by the formula [2a] to alkaline hydrolysis to produce a mixture comprising an optically active compound represented by the formula [3]
- wherein X is an alkali metal,
- and an optically active compound represented by the formula [3a]
- wherein X is an alkali metal;
- subjecting the optically active compound represented by the formula [3] to cyclization by adjusting the mixture comprising the optically active compound represented by the formula [3] and the optically active compound represented by the formula [3a] to pH 7.0 or lower with an acid to produce a mixture comprising an optically active compound represented by the formula [4]
- and an optically active compound represented by the formula [3b]
- and
- subjecting the mixture comprising the optically active compound represented by the formula [4] and the optically active compound represented by the formula [3b] to an extraction operation with an aromatic hydrocarbon solvent and a liquid separation operation to remove the optically active compound represented by the formula [3b] from the mixture comprising the optically active compound represented by the formula [4] and the optically active compound represented by the formula [3b].
Dependencies are inferred from the claim text.