CN110194735B - Visible light asymmetric catalytic synthesis method of chiral 3- (2-pyridine) -3-aryl substituted amine compound - Google Patents
Visible light asymmetric catalytic synthesis method of chiral 3- (2-pyridine) -3-aryl substituted amine compound Download PDFInfo
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
Abstract
Visible light asymmetric catalytic synthesis method of chiral 3- (2-pyridine) -3-aryl substituted amine compound, and synthesis methodThe route is as follows:
wherein the chiral spiro phosphonic acid and DPZ have the following structures:
under the atmosphere of argon gas, the reaction kettle is,Nthe method comprises the steps of completely reacting aryl-substituted glycine (I) with alpha-aryl-alpha- (2-pyridine) substituted terminal olefin (II) in THF or toluene at-35 to-40 ℃ under the irradiation of visible light by using DPZ, lithium hexafluorophosphate and chiral spiro phosphonic acid as catalysts, and carrying out column chromatography separation and purification to obtain a target chiral amine compound (III), wherein R in the compound I, the compound II and the compound III1= CN, H, F, Cl, Br, Ph or Me, R2= H, Me, Cl or Br, R3= H, F, Cl, Br, Me or MeO. The compound shown in the formula III is a chiral 3- (2-pyridine) -3-aryl substituted amine compound.
Description
Technical Field
The invention belongs to the field of synthesis of drug intermediates, and particularly relates to a visible light asymmetric catalytic synthesis method of a chiral 3- (2-pyridine) -3-aryl substituted amine compound.
Background
The chiral 3- (2-pyridine) -3-aryl substituted amine compound has wide application in the fields of synthetic drugs, natural products, functional materials and the like. In the research of green organic synthesis chemistry, the development of a method for synthesizing chiral 3- (2-pyridine) -3-aryl substituted amine compounds with environmental protection and high efficiency has important significance. The only reported methods for the synthesis of chiral 3- (2-pyridine) -3-aryl-substituted amines are transition metal catalyzed asymmetric hydrogenation of 3-aryl-3- (2-pyridine) -substituted allylamines (Botteghi, C.; Del Ponte, G.; Marchetti, C.J. mol. Catal.1993,83, L1; Marchetti, M.; Alberico, E.; Bertucci, C.; Botteghi, C.; Del Ponte, G.J. mol. Catal A: 1997,125, 109.). The catalytic system can generate hydrogenolysis yield of C-N bond of about 50% and optical purity of the product of less than 60%, so that the catalytic system cannot be used for high-stereoselectivity and high-yield synthesis of chiral 3- (2-pyridine) -3-aryl substituted amine compounds.
In recent years, the visible light catalytic reaction is widely applied to the field of organic synthesis due to greenness, high efficiency and mildness. Because the reaction condition has no heavy metal residue, the product does not need to be removed by heavy metal, and the visible light is used for catalyzing the conjugate addition-protonation reaction of the N-aryl substituted glycine and the alpha-aryl-alpha- (2-pyridine) substituted terminal olefin, so the method has a great application prospect.
Disclosure of Invention
The invention aims to provide a visible light asymmetric catalytic synthesis method of a chiral 3- (2-pyridine) -3-aryl substituted amine compound.
A visible light asymmetric catalytic synthesis method of chiral 3- (2-pyridine) -3-aryl substituted amine compounds comprises the following synthetic route:
wherein the chiral spiro phosphonic acid and DPZ have the following structures:
the synthesis process comprises the following steps: under the argon atmosphere, the N-aryl substituted glycine (I) and alpha-aryl-alpha- (2-pyridine) substituted terminal olefin (II) react completely in THF or toluene at-35 to-40 ℃ under the irradiation of visible light by using DPZ, lithium hexafluorophosphate and chiral spiro phosphonic acid as catalysts, and the target chiral amine compound (III) is obtained through column chromatography separation and purification, wherein R in the compound I, the compound II and the compound III1CN, H, F, Cl, Br, Ph or Me, R2H, Me, Cl or Br, R3H, F, Cl, Br, Me or MeO. Formula III shows a tetrahydroquinoline chiral 3- (2-pyridine) -3-aryl substituted amine compound. The product has important application value. Such as the reaction of 3- (2-pyridine) -3-benzeneThe radical-substituted amine is subjected to two-step chemical reaction to obtain the optically pure R-configuration fenpiramine antiallergic agent (pheniramine). The protective atmosphere is nitrogen or argon.
Preferably, R in compound I, compound II, compound III1H, F, Cl or Me, R2H or Br, R3H or MeO.
Further, the molar ratio of the compound I, the compound II, the DPZ, the chiral spirocyclic phosphonic acid and the lithium hexafluorophosphate is 1: 1-1.5: 0.002-0.003: 0.1-0.15: 0.3-0.5.
Further, when the reaction is carried out in the argon atmosphere, the reaction bottle filled with each reaction raw material needs to be vacuumized for at least three times, frozen (-70 to-80 ℃ for 3-5 min), restored to the room temperature, and filled with argon for protection.
Furthermore, the visible light is provided by a blue LED lamp with the power of 3W and the wavelength of 450-455nm, and the distance between the blue lamp and the reactant is 5-10 cm.
Further, the eluent for column chromatography separation and purification is composed of n-hexane and ethyl acetate in a volume ratio of 80-5: 1.
Compared with the prior art, the method has the beneficial effects that:
the method uses the DPZ photocatalyst without metal in the reaction, has the advantages of little catalyst consumption, high catalytic efficiency, mild reaction conditions, stability, high efficiency, simple operation, environmental protection, high product conversion rate, good selectivity, environmental protection and great popularization and application values.
Detailed Description
The technical solution of the present invention is further described in detail with reference to the following examples, but the scope of the present invention is not limited thereto.
In the following examples, the organic photocatalyst DPZ is described in the literature (Yu Zhao,
Chenhao Zhang,
kek Foo Chin, Old ˇ rich Pytela, Guo Wei, Hongjun Liu, Filip Bures and Zhiyong Jiang RSC adv.,2014,4, 30062). Chiral spirocyclic phosphonic acid CPA was purchased from the xylonite drug chiral technology (shanghai) ltd and lithium hexafluorophosphate was purchased from carbofuran.
Example 1
A visible light asymmetric catalytic synthesis method of chiral 3- (2-pyridine) -3-substituted amine compounds is disclosed, and the reaction formula is shown as follows. The specific preparation steps of (R) -N- (3-phenyl-3- (2-pyridyl) propyl) aniline are as follows:
wherein the chiral spiro phosphonic acid and DPZ have the following structures:
1 mg of DPZ organic photocatalyst was dissolved in 200. mu.L of toluene, 14.2. mu.L (0.0002mmol,0.002 eq.) were removed from the solution in a 25 mL Schlenk tube (Schlenk tube), and the toluene was blown dry using an air pump. Then adding 15.1 mg (0.1mmol) of N-phenylglycine (compound I), 21.7 mg (0.12mmol) of 2- (1-phenylalkenyl) pyridine (compound II), 9mg (0.015mmol) of chiral spiro phosphonic acid and 6mg (0.04mmol) of lithium hexafluorophosphate, then adding 4 ml of purified and dried tetrahydrofuran, vacuumizing the Schlenk tube for three times, freezing the tube at (-80 ℃) for 3min, recovering to room temperature, filling the tube into an argon shield, placing the Schlenk tube in a constant temperature box at-35 ℃, stirring for 60 hours under the irradiation condition of a 3W blue LED lamp (the wavelength is 450-455nm, the Schlenk tube is 5cm away from the LED lamp), after the reaction is finished, evaporating the tetrahydrofuran by using a rotary evaporator, directly carrying out column chromatography separation (the volume ratio of N-hexane/ethyl acetate is 80-5: 1) to obtain 25.1 mg of yellow solid compound III, the yield was 87% and the optical purity was 94% ee. The melting point is 67.2-68.9 ℃, and the nuclear magnetism data is as follows:1HNMR(300MHz,CDCl3)δ8.59(d,J＝4.3Hz,1H),7.57(td,J＝7.7,1.6Hz,1H),7.44-7.28(m,4H),7.25-7.07(m,5H),6.67(t,J＝7.3Hz,1H),6.53(d,J＝7.9Hz,2H),4.24(t,J＝7.7Hz,1H),3.74(s,1H),3.11(t,J＝7.0Hz,2H),2.61(dq,J＝14.4,7.1Hz,1H),2.40(dq,J＝14.3,7.2Hz,1H).)；13C NMR(75MHz,CDCl3) δ 163.3,149.2,148.3,143.3,136.5,129.1,128.6,128.0,126.6,122.9,121.4,117.1,112.7,51.3,42.3, 34.6; the high resolution data is: HRMS (ESI) M/z 311.1534(M + Na)+),calc.for C20H20N2Na 311.1524.
Example 2
The reaction formula for synthesizing (R) -N- (3-phenyl-3- (2-pyridyl) propyl) -4-methoxyaniline is shown below.
In this example, N-phenylglycine in example 1 was replaced with N- (p-methoxy-phenyl) glycine, and the other steps were carried out in the same manner as in example 1 to give (R) -N- (3- (4-methoxy-phenyl) -3- (2-pyridyl) propyl) aniline (26.4 mg) as a yellow oil in 83% yield and 94% ee in optical purity. The nuclear magnetic data are:1H NMR(300MHz,CDCl3)δ8.58(d,J＝4.2Hz,1H),7.56(td,J＝7.7,1.6Hz,1H),7.41-7.27(m,4H),7.24-7.06(m,3H),6.74(d,J＝8.8Hz,2H),6.50(d,J＝8.9Hz,2H),4.22(t,J＝7.7Hz,1H),3.73(s,3H),3.05(t,J＝7.0Hz,2H),2.57(dq,J＝14.5,7.1Hz,1H),2.38(td,J＝14.3,7.3Hz,1H)；13C NMR(75MHz,CDCl3) δ 163.2,151.8,149.1,143.2,142.4,136.5,128.5,127.9,126.5,122.8,121.4,114.7,114.0,55.7,51.1,43.2, 34.6; the high resolution data is: HRMS (ESI) M/z 341.1635(M + Na)+),calc.for C21H22N2ONa 341.1630.
Example 3
The reaction scheme for the synthesis of (R) -N- (3- (4-fluoro-phenyl) -3- (2-pyridyl) propyl) -aniline is shown below.
In this example, the 2- (1-phenylalkenyl) pyridine obtained in example 1 was replaced with 2- (1- (4-fluorophenylalkenyl) pyridine, and the other procedures were identical to those in example 1 to give (R) -N- (3- (4-fluoro-phenyl) -3- (2-pyridyl) propyl) -phenylamine 27.6mg as a yellow oil in 90% yield and 92% ee in optical purity. The nuclear magnetic data are:1H NMR(300MHz,CDCl3)δ8.59(d,J＝4.4Hz,1H),7.58(td,J＝7.8,1.5Hz,1H),7.37-7.28(m,2H),7.22-7.06(m,4H),6.99(t,J＝8.7Hz,2H),6.68(t,J＝7.3Hz,1H),6.53(d,J＝7.8Hz,2H),4.22(t,J＝7.7Hz,1H),3.61-3.01(m,3H),2.58(dq,J＝14.3,7.1Hz,1H),2.36(dq,J＝14.3,7.2Hz,1H)；13C NMR(75MHz,CDCl3)δ162.9,161.6(d,JF–C＝244.9Hz),149.2,148.1,138.9(d,JF–C＝3.1Hz),136.7,129.4(d,JF–C＝7.8Hz),129.2,122.9,121.6,117.2,115.4(d,JF–C21.2Hz),112.7,50.3,42.2, 34.7; the high resolution data is: HRMS (ESI) M/z 307.1613(M + H)+),calc.for C20H20N2F 307.1611.
Example 4
The reaction scheme for the synthesis of (R) -N- (3- (4-chloro-phenyl) -3- (2-pyridyl) propyl) -aniline is shown below.
In this example, the 2- (1-phenylalkenyl) pyridine obtained in example 1 was replaced with 2- (1- (4-chlorophenyl) alkenyl) pyridine, and the procedure was otherwise the same as in example 1 to give (R) -N- (3- (4-chloro-phenyl) -3- (2-pyridyl) propyl) -aniline (26.7 mg) as a yellow oil in 83% yield and 92% ee in optical purity. The nuclear magnetic data are:1H NMR(300MHz,CDCl3)δ8.54(d,J＝4.0Hz,1H),7.53(t,J＝7.6Hz,1H),7.24-7.16(d,J＝6.4Hz,4H),7.13-6.96(t,J＝7.3Hz,4H),6.63(t,J＝7.3Hz,1H),6.49(d,J＝7.9Hz,2H),4.16(t,J＝7.7Hz,1H),3.75(s,1H),3.04(t,J＝6.9Hz,2H),2.52(dq,J＝14.3,7.1Hz,1H),2.30(dq,J＝14.1,7.0Hz,1H)；13C NMR(75MHz,CDCl3) δ 162.5,149.2,148.0,141.7,136.7,132.3,129.3,129.2,128.7,122.9,121.7,117.3,112.7,50.4,42.1, 34.5; the high resolution data is:HRMS(ESI)m/z 323.1325(M+H+),calc.for C20H20N2Cl 323.1315.
example 5
The reaction scheme for the synthesis of (R) -N- (3- (3-fluoro-phenyl) -3- (2-pyridyl) propyl) -aniline is shown below.
In this example, the 2- (1-phenylalkenyl) pyridine obtained in example 1 was replaced with 2- (1- (3-fluorophenylalkenyl) pyridine, and the other procedures were identical to those in example 1 to give (R) -N- (3- (3-fluoro-phenyl) -3- (2-pyridyl) propyl) -phenylamine 27.8mg as a yellow oil in 91% yield and 91% optical purity ee. The nuclear magnetic data are:1H NMR(300MHz,CDCl3)δ8.57(d,J＝4.1Hz,1H),7.54(td,J＝7.7,1.6Hz,1H),7.21(t,J＝7.0Hz,1H),7.17-7.01(m,6H),6.87(td,J＝8.4,1.8Hz,1H),6.65(t,J＝7.3Hz,1H),6.51(d,J＝7.8Hz,2H),4.20(t,J＝7.7Hz,1H),3.65(s,1H),3.07(t,J＝7.0Hz,2H),2.55(dq,J＝14.6,7.1Hz,1H),2.33(dq,J＝14.1,7.2Hz,1H)；13CNMR(75MHz,CDCl3)δ162.4,162.9(d,JF–C＝245.9Hz),149.3,148.1,145.9(d,JF–C＝6.9Hz),136.6,129.9(d,JF–C＝8.3Hz),129.1,123.7(d,JF–C＝2.8Hz),122.9,121.7,117.2,114.8(d,JF–C＝21.5Hz),113.5(d,JF–C21.1Hz),112.7,50.8,42.1, 34.5; the high resolution data is: HRMS (ESI) M/z 307.1603(M + H)+),calc.for C20H20N2F 307.1611.
Example 6
The reaction scheme for the synthesis of (R) -N- (3- (4-methyl-phenyl) -3- (2-pyridyl) propyl) -aniline is shown below.
In this example, the 2- (1-phenylalkenyl) pyridine of example 1 was replaced with 2- (1- (4-methylbenzene) alkenyl) pyridine, and the other steps were conducted in the same manner as in example1 to give (R) -N- (3- (4-methyl-phenyl) -3- (2-pyridyl) propyl) -aniline, 26.9mg, as a yellow oil, in 89% yield and optical purity 92% ee. The nuclear magnetic data are:1H NMR(300MHz,CDCl3)δ8.61(d,J＝4.0Hz,1H),7.59(t,J＝7.1Hz,1H),7.40-7.27(m,2H),7.23-7.03(m,6H),6.70(t,J＝7.2Hz,1H),6.56(d,J＝7.8Hz,2H),4.23(t,J＝7.7Hz,1H),3.78(s,1H),3.13(t,J＝6.9Hz,2H),2.61(td,J＝14.0,6.9Hz,1H),2.50-2.27(m,4H)；13C NMR(75MHz,CDCl3) δ 163.5,149.1,148.2,140.2,136.5,136.2,129.3,129.1,127.8,122.8,121.4,117.0,112.7,50.8,42.3,34.5, 21.0; the high resolution data is: HRMS (ESI) M/z 325.1681(M + Na)+),calc.for C21H22N2Na 325.1681.
Example 7
The reaction scheme for the synthesis of (R) -N- (3- (2-methyl-phenyl) -3- (2-pyridyl) propyl) -aniline is shown below.
In this example, the 2- (1-phenylalkenyl) pyridine obtained in example 1 was replaced with 2- (1- (2-methylbenzene) alkenyl) pyridine, and the procedure was otherwise the same as in example 1 to give (R) -N- (3- (2-methyl-phenyl) -3- (2-pyridyl) propyl) -aniline (25.4 mg) as a yellow oil in 84% yield and 94% optical purity ee. The nuclear magnetic data are:1H NMR(300MHz,CDCl3)δ8.68(d,J＝4.5Hz,1H),7.63(td,J＝7.7,1.5Hz,1H),7.49(d,J＝7.5Hz,1H),7.36-7.26(m,2H),7.25-7.10(m,5H),6.76(t,J＝7.3Hz,1H),6.64(d,J＝7.9Hz,2H),4.60(t,J＝7.5Hz,1H),3.92(s,1H),3.25(t,J＝6.9Hz,2H),2.66(dq,J＝14.4,7.1Hz,1H),2.55-2.37(m,4H)；13C NMR(75MHz,CDCl3) δ 163.3,148.9,148.1,141.2,136.5,136.3,130.5,129.1,127.0,126.4,126.2,122.9,121.3,117.1,112.7,46.6,42.3,34.6, 20.0; the high resolution data is: HRMS (ESI) M/z 303.1864(M + H)+),calc.for C21H23N2 303.1861.
Example 8
The reaction scheme for the synthesis of (R) -N- (3-phenyl-3- (2- (4-bromo) -pyridinyl) propyl) -aniline is shown below.
In this example, the 2- (1-phenylalkenyl) pyridine obtained in example 1 was replaced with 2- (1-phenylalkenyl) - (4-bromo) -pyridine, and the other steps were the same as in example 1 to obtain (R) -N- (3-phenyl-3- (2- (4-bromo) -pyridyl) propyl) -aniline (26.8 mg) as a yellow solid, melting point 96.3-97.9 ℃, yield 73%, optical purity 91% ee. The nuclear magnetic data are:1H NMR(300MHz,CDCl3)δ8.40(d,J＝5.2Hz,1H),7.43-7.27(m,6H),7.26-.20(m,1H),7.15(t,J＝7.8Hz,2H),6.70(t,J＝7.3Hz,1H),6.56(d,J＝7.9Hz,2H),4.19(t,J＝7.6Hz,1H),3.11(t,J＝7.0Hz,2H),2.58(dq,J＝14.3,7.1Hz,1H),2.38(dq,J＝14.2,7.2Hz,1H)；13C NMR(75MHz,CDCl3) δ 164.7,149.9,147.7,142.4,133.2,129.2,128.8,127.9,126.9,126.3,124.9,117.6,113.0,50.9,42.4, 34.3; the high resolution data is: HRMS (ESI) M/z 367.0811(M + H)+),calc.for C20H20BrN2 367.0810.
The compound prepared in example 2 can be used to obtain the drug pheniramine (non-nilamin) by the reported method (2 steps), and the detailed first step of the following reactions can be referred to Joge M.M.Verkade, Lieke J.C.van Hemert, Peter J.L.M.Quaedflie, Paul L.Alters, Floris L.van Delft and Floris P.J.T.Rutjes.Mill and excipient deproporation of the amine protectngp-methoxyphennyl (PMP.tetrahedron Letters,2006,47: 8109-: taki, Masayasu; teramae, Shinichi; nagatomo, Shigenori; tachi, Yoshimitsu; kitagawa, Teizo; itoh, Shinobu; fukuzumi, Shuncihi, Fine-Tuning of hopper (I) -Dioxgen reaction by 2- (2-pyridol) ethyl amine Bidentate ligands, journal of the American Chemical Society 2002,124(22):6367-6377.
Claims (3)
1. A visible light asymmetric catalytic synthesis method of chiral 3- (2-pyridine) -3-aryl substituted amine compounds is characterized in that the synthesis route is as follows:
wherein the chiral spiro phosphonic acid and DPZ have the following structures:
under the protective atmosphere, the method comprises the following steps of,Nthe method comprises the steps of completely reacting aryl-substituted glycine (I) with alpha-aryl-alpha- (2-pyridine) substituted terminal olefin (II) in THF or toluene at-35 to-40 ℃ under the irradiation of visible light by using DPZ, lithium hexafluorophosphate and chiral spiro phosphonic acid as catalysts, and carrying out column chromatography separation and purification to obtain a target chiral amine compound (III), wherein R in the compound I, the compound II and the compound III1= CN, H, F, Cl, Br, Ph or Me, R2= H, Me, Cl or Br, R3H, F, Cl, Br, Me or MeO; the visible light is provided by a blue LED lamp with power of 3W and wavelength of 450-455 nm.
2. The method for the visible light asymmetric catalytic synthesis of the chiral 3- (2-pyridine) -3-aryl substituted amine compound according to claim 1, wherein the molar ratio of the compound I, the compound II, DPZ, the chiral spirocyclic phosphonic acid and the lithium hexafluorophosphate is 1: 1-1.5: 0.002-0.003: 0.1-0.15: 0.3-0.5.
3. The visible light asymmetric catalytic synthesis method of the chiral 3- (2-pyridine) -3-aryl substituted amine compound according to claim 1, wherein the eluent for column chromatography separation and purification is composed of n-hexane and ethyl acetate in a volume ratio of 80-5: 1.
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| CN104710377A (en) * | 2013-12-13 | 2015-06-17 | 中国科学院大连化学物理研究所 | Method for synthesizing chiral amine through biomimetic asymmetric hydrogenation |
| CN105001159A (en) * | 2014-04-23 | 2015-10-28 | 中国科学院大连化学物理研究所 | Method for synthesizing chiral cyclic amine through catalyzing asymmetric hydrogenation of quinolin-3-amine by chiral phosphoric acid |
| CN105175318A (en) * | 2015-07-29 | 2015-12-23 | 张燕梅 | Synthesis method of pheniramine maleate |
| CN105949079A (en) * | 2016-05-26 | 2016-09-21 | 河南大学 | Method for preparing N-(2-formyl phenyl) N-substituted formamide derivatives by means of visible light catalysis |
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