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A method for preparing pyrrolizidine skeleton from hydroxyproline and its derivatives

A proline and compound technology, which is applied in the field of preparing pyrrolizidine skeleton from hydroxyproline and its derivatives, can solve the problems of limited scope of application and limited research on synthetic methods

Active Publication Date: 2022-01-11
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Based on the relevant literature, it can be seen that the research on the synthesis method of pyrrolizidine is very limited, often using multi-step synthesis methods or involving expensive metals as catalysts, and the scope of application is extremely limited

Method used

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  • A method for preparing pyrrolizidine skeleton from hydroxyproline and its derivatives
  • A method for preparing pyrrolizidine skeleton from hydroxyproline and its derivatives
  • A method for preparing pyrrolizidine skeleton from hydroxyproline and its derivatives

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0041] cis-6,7,8,8a-tetrahydro-4aH-pyrrolo[1,2-a]indol-9(5H)-one,Ⅲaa,ab,ac.

[0042]

[0043] 1 H NMR (400MHz, CDCl 3 )δ7.06–7.00(m,1H),6.70(d,J=3.9Hz,1H),6.49(dd,J=3.9,2.3Hz,1H),4.59(dd,J=12.8,7.0Hz,1H ),3.12(dd,J=11.9,6.9Hz,1H),2.24–2.04(m,2H),1.86–1.73(m,1H),1.53(m,2H),1.48–1.31(m,3H). 13 C NMR (101MHz, CDCl 3 )δ191.9, 131.8, 121.7, 116.1, 107.5, 54.1, 50.2, 30.1, 22.5, 20.8, 19.5. HRMS (ESI) m / z Calcd for C 11 h 13 NO(M+H + ):175.0997,found:175.0995.Light yellow oil.

example 2

[0045] cis-5,6,7,8,9,9a-hexahydrocyclohepta[b]pyrrolizin-10(4H)-one,Ⅲba.

[0046]

[0047] 1 H NMR (400MHz, CDCl 3 )δ7.01(s,1H),6.71(d,J=3.9Hz,1H),6.53(dd,J=3.6,2.4Hz,1H),4.69(td,J=8.7,3.6Hz,1H), 3.34–3.19(m,1H),2.18(m,1H),2.13–1.82(m,3H),1.70(m,2H),1.46(d,J=9.8Hz,4H). 13 C NMR (101MHz, CDCl 3 )δ192.05, 132.63, 121.24, 116.78, 107.11, 59.42, 55.76, 32.93, 30.80, 27.77, 27.63, 24.89. HRMS (ESI) m / z Calcdfor C 12 h 15 NO(M+H + ):190.1232,found:190.1228.Light yellow oil.

example 3

[0049] cis-ethyl10-oxo-4a,5,6,7,8,9,9a,10-octahydrocyclohepta[b]pyrrolizine-7-carboxylate,Ⅲca.

[0050]

[0051] 1 H NMR (400MHz, CDCl 3 )δ7.04(s,1H),6.72(d,J=3.8Hz,1H),6.53(d,J=14.5Hz,1H),4.71–4.61(m,1H),4.19–4.10(q,J =7.1Hz,2H),3.31–3.20(m,1H),2.47–2.28(m,3H),2.25–2.15(m,1H),2.11–2.00(m,1H),1.81(m,2H), 1.72–1.63(m,2H),1.27(t,J=7.0Hz,3H). 13 C NMR (101MHz, CDCl 3 )δ191.05, 175.14, 132.08, 121.40, 117.07, 107.56, 60.55, 59.34, 55.81, 46.90, 30.78, 30.60, 27.69, 25.49, 14.22. HRMS (ESI) m / z Calcd for C 15 h 19 NO 3 (M+H + ):262.1443,found:262.1439.Light yellow solid.

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Abstract

The invention relates to a method for preparing pyrrolizidine skeleton from hydroxyproline and its derivatives, and relates to a method for preparing pyrrolizidine derivatives, the main steps of which are: in the presence of an acidic catalyst, by Ketone I reacts with 4-substituted-L-proline II in a reaction medium at 60°C to 160°C to obtain the target pyrrolizidine derivative. The method has mild conditions, no inert gas protection, simple operation, high atom utilization rate, wide range of substrate applications, suitable for industrial scale-up, and has good industrialization prospects.

Description

technical field [0001] The invention belongs to the technical field of chemical pharmacy and fine chemical preparation, that is, one-pot method for preparing pyrrolizidine alkaloids, especially the process does not involve metal catalysis, and the most important thing is that the amino acids participating in the reaction do not need to be pre-activated or added activation reagents, carboxyl The acid directly participates in the Clasien condensation reaction to efficiently generate a polyfunctional group-substituted pyrrolizidine alkaloid structure. The invention provides a feasible technical route and design strategy for efficiently preparing functionalized pyrrolizidine alkaloid derivatives, and has wide application in the fields of chemical, pharmaceutical and fine chemical industries. Background technique [0002] Pyrrolizidine Alkaloids (PAs, 1) is an important class of alkaloids with a pyrrolizidine structure, which exists in a variety of plants and is used to resist in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04C07B2200/07
Inventor 虞心红唐蜜郑紫薇胡杨孙仍蔚宋广军章慧文李旭彬
Owner EAST CHINA UNIV OF SCI & TECH