1H-1,2,4-Triazole → 1-{[3-(2-Methyl-1,3-dioxolan-2-yl) tricyclo [3.3.1.03,7]non-1-yl]methyl}-1H-1,2,4-triazole

HRID 1015530노트

반응식

HRID 1015530 반응식
CS(O[CH2:6][C:7]12[CH2:15][CH:11]3[CH2:12][CH:13]([CH2:14]1)[C:9]([C:16]1([CH3:21])[O:20][CH2:19][CH2:18][O:17]1)([CH2:10]3)[CH2:8]2)(=O)=O.C([O-])([O-])=O.[K+].[K+].[NH:28]1[CH:32]=[N:31][CH:30]=[N:29]1>CN(C=O)C.O>[CH3:21][C:16]1([C:9]23[CH2:10][CH:11]4[CH2:15][C:7]([CH2:6][N:28]5[CH:32]=[N:31][CH:30]=[N:29]5)([CH2:14][CH:13]2[CH2:12]4)[CH2:8]3)[O:17][CH2:18][CH2:19][O:20]1

참가 물질

6

반응물 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 59374979[3-(2-Methyl-1,3-dioxolan-2-yl) tricyclo[3.3.1.03,7]non-1-yl]methyl methane sulfonate

생성물 1

HCID 673004551-{[3-(2-Methyl-1,3-dioxolan-2-yl) tricyclo [3.3.1.03,7]non-1-yl]methyl}-1H-1,2,4-triazole수율 85%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

A stirred mixture of [3-(2-Methyl-1,3-dioxolan-2-yl)tricyclo[3.3.1.03,7]non-1-yl]methyl methanesulfonate (2.4 g, 7.5 mmol) [as obtained from preparation 2], K2CO3 (4.5 g, 34.2 mmol), and 1,2,4-triazole (1.5 g, 22.5 mmol) in DMF (30 mL) was heated to 110° C. for 5 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethylacetate. The combined organic layer was washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography to obtain 1-{[3-(2-Methyl-1,3-dioxolan-2-yl)tricyclo[3.3.1.03,7]non-1-yl]methyl}-1H-1,2,4-triazole (1.82 g) as a viscous liquid in 85% yield. m/z (M+1) 290; IR cm−1 2932, 1668, 1506, 1441, 1373, 1311, 1211, 1140, 1047, 876, 753. 1H NMR (CDCl3) 300 MHz δ 7.99 (s, 1H), 7.93 (s, 1H), 4.07 (s, 2H), 4.03-3.92 (m, 4H), 2.42-2.32 (m, 2H), 1.86-1.79 (m, 1H), 1.74-1.65 (m, 2H), 1.52-1.37 (m, 8H), 1.26 (s, 3H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethylacetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-88fd6a2a52f046649bd19c99348fca8b
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985759B2

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