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Preparation method of octahydro dipyrroloquinoline compound

A technology for octahydrodipyrrole and compound, which is applied in the field of preparation of octahydrodipyrroloquinoline compounds, can solve the problems of pollution, high cost of chiral phosphoric acid and silver catalyst, and achieves the effect of low cost

Active Publication Date: 2018-04-20
QINGDAO AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The catalysts used are: The method uses chiral phosphoric acid and silver catalysts with high cost and pollution

Method used

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  • Preparation method of octahydro dipyrroloquinoline compound
  • Preparation method of octahydro dipyrroloquinoline compound
  • Preparation method of octahydro dipyrroloquinoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 3-methoxyphenyl-2-pyrrolidinyl-1-ylphenylmethanol As an example, to prepare The reaction process is shown in Table 1,

[0023] 0.2mmol After being mixed with catalyst (20mol%), add in the solvent of 2ml, react under the condition of 60 ℃, reaction time is as shown in the table, check the productive rate of final product, the result is shown in table 1.

[0024] Table 1: Reaction conditions and results

[0025]

[0026] In 17 in Table 1, DCE is dried first, and the drying method is: add CaH to each liter of DCE 2 5g, distilled at 130°C; b : Column chromatography separation yield.

Embodiment 2

[0028] raw material: 3-methoxyphenyl-2-pyrrolidinyl-1-ylphenylcarbinol

[0029] Reaction conditions: Toluene, 60°C, PA (20%)

[0030] Product: Chemical formula: C 36 h 38 N 2 o 2

[0031] Exact molecular weight: 530.2933

[0032] Molecular weight: 530.7120

[0033] Structural formula:

[0034] Yield: 96%, dr 5:1.

[0035] 1 H NMR (500MHz, CDCl 3 )δ7.15(dt, J=14.9, 7.7Hz, 4H), 7.04–6.96(m, 2H), 6.79–6.62(m, 9H), 6.50(t, J=7.5Hz, 1H), 4.80(d ,J=8.4Hz,1H),4.06(s,2H),3.94–3.81(m,3H),3.74(d,J=12.0Hz,6H),3.65(dd,J=10.2,5.4Hz,2H) ,3.53(dd,J=16.1,7.9Hz,1H),3.42(td,J=8.5,4.0Hz,1H),3.20(td,J=8.7,2.7Hz,1H),2.89(dd,J=15.8 ,8.4Hz,1H),2.73(td,J=10.6,2.9Hz,1H),2.07–2.00(m,1H),1.98–1.74(m,6H); 13 C NMR (125MHz, CDCl 3 )δ159.65,159.56,150.33,145.68,143.65,143.38,137.12,131.00,130.68,129.17,129.09,127.94,127.78,127.16,127.01,123.26,122.30,121.81,121.24,118.45,114.95,114.49,111.09,111.02,63.78 ,59.70,55.12,55.07,53.67,52.26,42.71,39.90,37.45,29.07,25.84,24.50; HRMS(ESI):calcd ...

Embodiment 3

[0037] raw material: 4-Methoxyphenyl-2-pyrrolidin-1-ylphenylcarbinol

[0038] Reaction conditions: Toluene, 60°C, PA (20%)

[0039] Product: Chemical formula: C 36 h 38 N 2 o 2

[0040] Exact molecular weight: 530.2933

[0041] Molecular weight: 530.7120

[0042] Structural formula:

[0043] Yield: 92%, dr 5:1.

[0044] 1 H NMR (500MHz, CDCl 3 )δ7.20–7.15(m,1H),7.12(d,J=7.2Hz,1H),7.01(dd,J=9.0,5.2Hz,4H),6.99(dd,J=5.3,2.0Hz,2H ),6.80–6.78(m,1H),6.78–6.73(m,4H),6.65(dd,J=9.1,3.7Hz,1H),6.49(t,J=7.5Hz,1H),4.79(d, J=8.5Hz, 1H), 4.02(d, J=5.2Hz, 2H), 3.88(dd, J=10.6, 7.7Hz, 1H), 3.80–3.76(m, 1H), 3.74(d, J=6.0 Hz, 6H), 3.72(d, J=5.3Hz, 1H), 3.65–3.60(m, 1H), 3.52(dd, J=16.3, 7.8Hz, 1H), 3.42(td, J=8.6, 4.1Hz ,1H),3.23–3.18(m,1H),2.89(dt,J=8.7,6.9Hz,1H),2.72(qd,J=8.3,3.2Hz,1H),2.06–1.98(m,1H), 1.96–1.73(m,6H); 13 C NMR (125MHz, CDCl 3 )δ157.73,157.71,150.23,145.76,137.81,133.98,133.85,130.94,130.62,130.23,129.65,127.72,127.69,127.07,123.27,122.27,118.44,113.72,113...

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Abstract

The invention provides a method for producing an octahydro dipyrroloquinoline compound by using a phenyl-2-pyrrolidinyl benzyl alcohol compound under the acid condition. The phenyl-2-pyrrolidinyl phenylmethanol compound is dewatered under the acid condition to produce carbon positive ions; hydrogen on the tetrahydropyrrole ortho carbon is migrated to the carbon positive ions in a hydrogen anion form; imine positive ions are produced in situ; one part of imine positive ions are converted into enamine through proton transfer; enamine molecules and molecules containing the imine positive ions take intermolecular [4+2] ring addition reaction to obtain the octahydro dipyrroloquinoline compound. The building of the octahydro dipyrroloquinoline compound through a hydrogen migration strategy is realized; metal catalysts are not needed; green and environment-friendly effects are realized; the cost is low.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of octahydrodipyrroloquinoline compounds. Background technique [0002] The octahydrodipyrroloquinoline skeleton is a diastereomer of the basic skeletons of the natural products Incargranine B and seneciobipyrrolidine. [0003] [0004] Currently, the methods for producing similar framework compounds are as follows: [0005] The catalysts used are: The method uses chiral phosphoric acid and silver catalysts with high cost and pollution. Contents of the invention [0006] Aiming at the problems existing in the prior art, the object of the present invention is to provide a method for generating octahydrodipyrroloquinoline compounds from phenyl-2-pyrrolidinyl benzyl alcohol compounds under acidic conditions. [0007] Concrete reaction formula is as follows: [0008] [0009] Among them, R1, R2, R3 are H, CH 3 or OCH 3 . [0010] The ...

Claims

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Application Information

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IPC IPC(8): C07D471/14
CPCC07D471/14
Inventor 肖建朱帅李帅帅王亮
Owner QINGDAO AGRI UNIV
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