Реакция #1098654

Уравнение реакции

10

2-Nitro-1-(prop-2-ynyl)-1H-imidazole

29

2-Azido-3-fluoropropan-1-ol

THF

sodium ascorbate

→

1

Выход 88.1%

3-Fluoro-2-(4-((2-nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)propan-1-ol

Выход 88.1%

Растворители

t-BuOH

H2O

Условия реакции

Обработка

1. 1
   ДругоеOrganic solvents removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue dissolved in CH2Cl2
3. 3
   Промывкаconsecutively washed with H2O
4. 4
   Сушкаbrine, then dried over MgSO4
5. 5
   КонцентрированиеThe solvent was then concentrated in vacuo
6. 6
   Другоеthe residue was purified on silica gel using 10% MeOH

Методика

A solution of 10 (1.9 g, 12.6 mmol) and 29 (1.5 g, 12.6 mmol) in t-BuOH:THF:H2O (22.5 mL, 1:1:1) was treated with CuSO4.5H2O (0.31 g, 1.26 mmol) and sodium ascorbate (0.5 g, 2.52 mmol) and stirred for 1 hr at room temperature. Organic solvents removed under vacuum, the residue dissolved in CH2Cl2 and consecutively washed with H2O, then brine, then dried over MgSO4. The solvent was then concentrated in vacuo and the residue was purified on silica gel using 10% MeOH:CH2Cl2 as the solvent to afford 1 (3.00 g, 88%) as white solid. The product was further purified via recrystallization from EtOAc/hexanes. 1H NMR ((CD3)2CO, 400 MHz) δ: 8.15 (s, 1H), 7.57 (d, J=1.2 Hz, 1H), 7.11 (d, J=1.2 Hz, 1H), 5.79 (s, 2H), 4.87-5.05 (m, 2H), 4.82 (dd, J=4.0, 10.0 Hz, 1H), 4.17-4.45 (m, 1H), 4.03 (t, J=5.6 Hz, 2H). 13C NMR ((CD3)2CO, 100 MHz) δ: 141.8, 127.9, 127.1, 123.5, 83.0, 81.3, 63.0 (d, J=18.69 Hz, 1C), 60.5 (d, 6.73 Hz, 1C), δ: 44.8; 19F NMR ((CD3)2CO, 376 MHz) 230.2 (ddd, J=19.18, 19.55, 21.60 Hz, 1F); Mass Spec (lo-res): Calc'd for C9H11FN6O3: 270.09; found: 271.1 (M+H).

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