Method for synthesizing chiral Tr*ger's base derivatives
A derivative and chiral technology, applied in the new synthesis field of chiral base derivatives, can solve the problem of high cost, and achieve the effects of short reaction time, simple post-processing and mild reaction conditions.
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Embodiment 1
[0039] 5,12-Dimethyl-3,10-diphenyl-bis-1H-pyrazole[b,f][4,5]-1,5-diazabicyclo[3.3.1]-2,6 -The synthesis of octadiene (TB1), its reaction formula is as follows:
[0040]
[0041] In a 25mL round bottom flask, add 5-amino-3-methyl-1-phenyl-1H-pyrazole (2mmol), paraformaldehyde (6mmol) and [Py-G] + [BF 4 ] - (2mL), under argon protection, 2.0mL trifluoroacetic acid was added dropwise, stirred at room temperature for 5h, after the reaction was complete (TLC tracking), 10mL distilled water was added, suction filtered, and the solid crude product was subjected to column chromatography V 石油醚 :V 乙酸乙酯 =5:1, TB1 is obtained. Yield: 83%. M.p.: 266-267°C, white solid. ee 99%, (determined by HPLC analysis Chiralcel OD-H column, IPA:hexane=15:85), retention time: t minor =7.79min,t major =13.45min. 1 H NMR (400MHz, DMSO-d 6 )δ7.95-7.97(d, J=8.4Hz, 4H), 7.49-7.53(m, 4H), 7.30-7.32(t, J=8.0Hz, 2H), 4.24-4.32(t, J=7.2Hz , 4H), 3.59 (d, J=15.6Hz, 2H), 1.97 (s, 6H). HRMS (ESI) m / z:...
Embodiment 2
[0043]5,12-bis(4-methyl-phenyl)-3,10-diphenyl-bis-1H-pyrazole[b,f][4,5]-1,5-diazabicyclo[3.3 .1]-2, the synthesis of 6-octadiene (TB2), its reaction formula is as follows:
[0044]
[0045] In a 25mL round bottom flask, add 5-amino-3-(4-methylphenyl)-1-phenylpyrazole (2mmol), paraformaldehyde (6mmol) and [Py-G] + [BF 4 ] - (2mL), under argon protection, 2.0mL trifluoroacetic acid was added dropwise, stirred at room temperature for 7h, after the reaction was complete (TLC tracking), 10mL distilled water was added, suction filtered, and the solid crude product was subjected to column chromatography V 石油醚 :V 乙酸乙酯 =5:1, TB2 is obtained. Yield: 83%. M.p.: 266-267°C, white solid. Yield: 83%. M.p.283-284°C, white solid. ee 99% (determined by HPLC analysis Chiralcel OD-H column, IPA: hexane = 15: 85), retention time: t minor =7.66min,t major =13.26min. 1 H NMR (400MHz, DMSO-d 6 )δ8.07-8.09(d, J=8.0Hz, 4H).7.60-7.64(m, 4H), 7.44-7.46(m, 6H), 7.23-7.25(d, J=8.0Hz, 4H), 4....
Embodiment 3
[0047] 5,12-bis(4-methoxy-phenyl)-3,10-diphenyl-bis-1H-pyrazole[b,f][4,5]-1,5-diazabicyclo[ 3.3.1]-2, the synthesis of 6-octadiene (TB3), its reaction formula is as follows:
[0048]
[0049] In a 25mL round bottom flask, add 5-amino-3-(4-methoxyphenyl)-1-phenylpyrazole (2mmol), paraformaldehyde (6mmol) and [Py-G] + [BF 4 ] - (2mL), under argon protection, 2.0mL trifluoroacetic acid was added dropwise, stirred at room temperature for 7h, after the reaction was complete (TLC tracking), 10mL distilled water was added, suction filtered, and the solid crude product was subjected to column chromatography V 石油醚 :V 乙酸乙酯 =5:1, TB3 is obtained. Yield: 73%. M.p.>300°C, white solid. ee 79% (determined by HPLC analysis Chiralcel OD-H column, IPA: hexane = 15: 85), retention time: t minor =8.73min,t major =16.67min. 1 H NMR (400MHz, DMSO-d 6 )δ8.01-8.03 (d, J=8.0Hz, 4H).7.53-7.57 (m, 4H), 7.36-7.44 (m, 6H), 6.93-6.95 (d, J=8.0, 4H), 4.71- 4.75(d, J=8.4Hz, 2H), 4.54(s, 2H), 3....
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