Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of preparation method of chiral trifluoromethyl allylamine compound

A technology of trifluoromethylallylamine and trifluoromethylallyl sulfinamide, which is used in the preparation of pharmaceuticals, chemical intermediates, the preparation of chiral trifluoromethylallylamine compounds, and pesticides. It can solve the problems of low yield and complex process of trifluoromethylallylamine compounds, and achieve the effects of short reaction time, significant technological progress and good application prospects.

Active Publication Date: 2017-12-01
CHINA GATEWAY PHARMA DEV CO LTD
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the above-mentioned technical problems in the prior art, the present invention provides a method for preparing chiral trifluoromethylallylamine compounds, the chiral trifluoromethylallylamine compounds are The preparation method solves the technical problems of complex process and low yield in the synthesis of trifluoromethylallylamine compounds containing four-substituted carbon chiral centers in the prior art

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of preparation method of chiral trifluoromethyl allylamine compound
  • A kind of preparation method of chiral trifluoromethyl allylamine compound
  • A kind of preparation method of chiral trifluoromethyl allylamine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Under nitrogen protection, add 2 mL of anhydrous tetrahydrofuran and unsaturated imine to the reaction tube (62.3mg, 0.2mmol), CsF (34mg, 0.22mmol) was cooled to 0°C, TMSCF was added 3 Reagent (143.2mg, 1mmol), after the completion, the reaction was incubated, stirred, and TLC followed the reaction until it was complete. Add 5 ml of saturated aqueous ammonium chloride solution. The liquid was separated, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the product was obtained by flash column chromatography 74.7 mg, yield 98%.

[0030] 1 H NMR (400MHz, CDCl 3 ):δ7.21-7.86(m,10H),7.04(d,J=16.2Hz,1H),6.63(d,J=16.2Hz,1H),4.12(s,1H),1.28(s,9H) ; 19 F NMR (376MHz, CDCl 3 ):δ-73.59(s,3F); 13 C NMR (101MHz, CDCl 3 ): δ135.63, 135.32, 133.93, 129.38, 129.35, 128.71, 128.60, 128.41, 127.01, 125.98, 125.39 (q, J = 286.6 Hz), 69.13 (q, J = 27.0 Hz), 57.27, 22.68.

Embodiment 2

[0032] Under nitrogen protection, add 2 mL of anhydrous tetrahydrofuran and unsaturated ketimine to the reaction tube (68.3mg, 0.2mmol), CsF (34mg, 0.22mmol) was cooled to 0°C, TMSCF was added 3 Reagent (143.2mg, 1mmol), after the completion, the reaction was incubated, stirred, and TLC followed the reaction until it was complete. Add 5 ml of saturated aqueous ammonium chloride solution. The liquid was separated, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the product was obtained by flash column chromatography 41.2 mg, 50% yield.

[0033] 1 H NMR (400MHz, CDCl 3 ):δ7.22-7.59(m,7H),7.05(d,J=16.3Hz,1H),6.92(d,J=8.9Hz,2H),6.61(d,J=16.3Hz,1H),4.09 (s,1H),3.82(s,3H),1.27(s,9H); 19 F NMR (376MHz, CDCl 3 ):δ-73.99(s,3F); 13 C NMR (101MHz, CDCl 3 ), 57.13, 55.26, 22.74.

Embodiment 3

[0035] Under nitrogen protection, add 2 mL of anhydrous tetrahydrofuran and unsaturated ketimine to the reaction tube (69.2mg, 0.2mmol), CsF (34mg, 0.22mmol) was cooled to 0°C, TMSCF was added 3 Reagent (143.2mg, 1mmol), after the completion, the reaction was incubated, stirred, and TLC followed the reaction until it was complete. Add 5 ml of saturated aqueous ammonium chloride solution. The liquid was separated, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the product was obtained by flash column chromatography 66.5 mg, 80% yield.

[0036] 1 H NMR (400MHz, CDCl 3 ):δ7.25-7.70(m,9H),7.02(d,J=16.3Hz,1H),6.59(d,J=16.3Hz,1H),4.11(s,1H),1.28(s,9H) ; 19 F NMR (376MHz, CDCl 3 ):δ-73.80(s,3F); 13 C NMR (101MHz, CDCl 3 ), 57.37, 22.69.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the technical field of organic chemistry, and provides a preparation method of a chiral trifluoromethyl allyl amine compound. The method comprises the steps that optically pure alpha, beta-unsaturated tertiary butyl sulphinyl ketimine and a commercial Ruppert-Prakash reagent are utilized to serve as the raw materials, and under the protection of inert gas and catalysis of a Lewis base, the trifluoromethyl allyl amine compound which is prone to conversion and derivatization and contains a tetra-substituted carbon chiral center is obtained by means of a direct asymmetric trifluoromethylation reaction of position selectivity, high yield and excellent diastereoselectivity. According to the reparation method of the chiral trifluoromethyl allyl amine compound, the raw materials are convenient and easy to obtain, operation of a synthetic method is easy, the reaction time is short, the yield and optical purity of a product are high, the method for preparing the trifluoromethyl allyl amine compound containing the tetra-substituted carbon chiral center is universal, and good application prospect is achieved.

Description

technical field [0001] The invention belongs to the field of organic chemistry, in particular to a method for preparing medicine, pesticide and chemical intermediates, in particular to a method for preparing chiral trifluoromethylallylamine compounds. Background technique [0002] Chiral trifluoromethylallylamine compounds are a very important class of organic compounds. This structural unit not only widely exists in some medicines, pesticides, materials and other molecules ((a) Ojima, I.; McCarthy, J.R. ; Welch, J.T. Biomedical Frontiers of Fluorine Chemistry; ACS Symposium Series, No.639; American Chemical Society: Washington, DC, 1996. (b) Filler, R.; Kobayashi, Y.; Applications; Elsevier: Amsterdam, 1993. (c) Fluorine in Bioorganic Chemistry; Welch, J.T., Eshwarakrishman, S., Eds.; Wiley: New York, NY, 1991.), and because it contains a variety of functional groups, it is also a synthetic multifunctional important intermediates of various useful compounds (Liu, P.; Liu, ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C313/06C07D307/52C07C209/62C07C211/29
CPCC07B2200/07C07C209/62C07C313/06C07D307/52C07C211/29
Inventor 刘振江刘朋杨志强吴范宏岳朝颖
Owner CHINA GATEWAY PHARMA DEV CO LTD
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com