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Preparation method of cyclopentenone and cyclopentenone for synthesizing benzindene prostaglandins

A technology of cyclopentenone and phenyl, which is applied in the direction of preparation of heterocyclic compounds, chemical instruments and methods, compounds of group 4/14 elements of the periodic table, etc., can solve problems such as expensive, low yield, and not easy to obtain

Active Publication Date: 2016-01-20
CHIROGATE INT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, the yield of this preparation method was as low as 10%
Furthermore, the starting material of formula A used in this preparation is relatively expensive and not readily available, since under normal circumstances this starting material would be synthesized in an 11-step process as shown in Scheme 2 below, to the expensive formula C [Organic Chemistry (J.Org.Chem.), 53,23,5590 (1994); JP07252276]

Method used

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  • Preparation method of cyclopentenone and cyclopentenone for synthesizing benzindene prostaglandins
  • Preparation method of cyclopentenone and cyclopentenone for synthesizing benzindene prostaglandins
  • Preparation method of cyclopentenone and cyclopentenone for synthesizing benzindene prostaglandins

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0060] 1-(furan-2-yl)-2-(3-methoxyphenyl)ethan-1-one

[0061]

[0062] 3-Methoxyphenylacetic acid (20 g, 120.35 mmol) was dissolved in CH 2 Cl 2 (200 mL), and to the solution were added furan (24.6 g, 361.39 mmol) and trifluoroacetic anhydride (37.8 g, 180 mmol). The reaction was kept stirring overnight at room temperature. with saturated NaHCO 3 The reaction was quenched until pH = 6.9, and the organic reagents in the mixture were evaporated. The residue was extracted with EtOAc, and the organic layer was washed with brine, washed over MgSO 4 Dry and evaporate. The resulting residue was purified by silica gel column chromatography using hexane-EtOAc as eluent to afford 1-(furan-2-yl)-2-(3-methoxyphenyl)ethane-1- as a yellow oil Ketone: 20g (yield: 77%)

[0063] 1 HNMR (300MHz, CDCl 3)δ3.76(3H,s),4.07(2H,s),6.50(1H,dd,J=1.7,3.6Hz),6.76-6.89(3H,m),7.19-7.26(2H,m),7.57 (1H,dd,J=0.7,1.7Hz).

example 2

[0065] 1-(furan-2-yl)-2-(3-benzyloxyphenyl)ethan-1-one

[0066]

[0067] 3-Benzyloxyphenylacetic acid (3.5kg, 14.45mol) was dissolved in CH 2 Cl 2 (35 L), and furan (3.0 kg, 44 mol) and trifluoroacetic anhydride (4.55 kg, 21.65 mol) were added to the solution. The reaction was kept stirring at room temperature for 2 days. with saturated NaHCO 3 The reaction was quenched until pH = 6.9, and the organic reagents in the mixture were evaporated. The residue was extracted with EtOAc, and the organic layer was washed with brine, washed over MgSO 4 Dry and evaporate. The resulting residue was purified by silica gel column chromatography using hexane-EtOAc as eluent to afford 1-(furan-2-yl)-2-(3-benzyloxyphenyl)ethane-1 as a yellow oil - Ketone: 4kg (yield: 95%)

[0068] 1 HNMR (300MHz, CDCl 3 )δ4.08(2H,s),5.03(2H,s),6.50(1H,dd,J=1.71,3.59Hz),6.86-6.97(3H,m),7.19-7.44(7H,m),7.51 (1H,dd,J=0.76,1.7Hz)

[0069] 13 CNMR (75MHz, CDCl 3 )δ45.3, 69.8, 112.3, 113.3, 115.9, 118...

example 3

[0071] 1-(furan-2-yl)-2-(3-methoxyphenyl)ethan-1-ol

[0072]

[0073] 1-(furan-2-yl)-2-(3-methoxyphenyl)ethan-1-one (20 g, 92.56 mmol) was dissolved in MeOH (200 mL) and slowly added to the solution at 5 °C Add NaBH 4 (3.5 g, 92.52 mmol). After the reaction is complete, use H 2 The solution was quenched with O, and MeOH was evaporated. The residue was extracted with EtOAc and the organic layer was washed with brine, washed over MgSO 4 Drying and evaporation gave 1-(furan-2-yl)-2-(3-methoxyphenyl)ethan-1-ol as a yellow oil: 20 g (crude yield: 98%)

[0074] 1 HNMR (300MHz, CDCl 3 )δ2.12(1H,s),3.15(2H,m),3.79(3H,s),4.93(1H,s),6.25(1H,s),6.35(1H,s),6.74(1H,s ),6.81(2H,m),7.23(1H,t,J=7.9Hz),7.43(1H,s)

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Abstract

The invention relates to a preparation method of cyclopentenone and cyclopentenone used for synthesizing benzindene prostaglandins. The present invention provides novel processes for the preparation of racemic and optically active cyclopentenones of formula I: The present invention also provides novel cyclopentenones of formula I in racemic or optically active form.

Description

technical field [0001] The present invention relates to a novel process for the preparation of cyclopentenones of formula I, [0002] [0003] Said cyclopentenones are suitable for the preparation of the corresponding benzindene prostaglandins. The present invention also relates to novel cyclopentenones prepared by said process. Background technique [0004] Benzoindene prostaglandins are known to be useful in the treatment of a variety of conditions. Formula I cyclopentenone [0005] [0006] where P 1 is a phenolic protecting group, also disclosed in a co-pending patent application filed on the same date and titled "INTERMEDIATESFORTHESYNTHESISOFBENZINDENEPROSTAGLANDINSANDPREPARATIONSTHEREOF" for the synthesis of benzindene prostaglandins The key intermediate of the element. No racemic or optically active cyclopentenones of formula I are disclosed in the prior art. As shown in Scheme 1 below, Sato disclosed an optically active cyclopentenone of formula B and it...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/753C07C45/59C07F7/18C12P41/00C12P7/38
CPCC07C45/59C12P7/22C12P7/26C12P41/004Y02P20/55C07C49/753C07C45/78C07C49/395C07D307/28
Inventor 魏士益张婉君叶有芝
Owner CHIROGATE INT
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