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 1015530Notes

Reaction equation

HRID 1015530 reaction equation
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

Participants

6

Reactant 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

Product 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-triazoleYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-88fd6a2a52f046649bd19c99348fca8b
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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