Reaktion #1244279

Reaktionsgleichung

10

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

29

2-Azido-3-fluoropropan-1-ol

THF

sodium ascorbate

→

1

Ausbeute 88.1%

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

Ausbeute 88.1%

Lösungsmittel

t-BuOH

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeOrganic solvents removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue dissolved in CH2Cl2
3. 3
   Waschenconsecutively washed with H2O
4. 4
   Trocknenbrine, then dried over MgSO4
5. 5
   EinengenThe solvent was then concentrated in vacuo
6. 6
   Sonstigethe residue was purified on silica gel using 10% MeOH

Vorschrift

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, J=6.73 Hz, 1C), δ: 44.8; 19F NMR ((CD3)2CO, 376 MHz) 230.2 (ddd, J=19.18, 19.55, 21.60 Hz, IF); Mass Spec (lo-res): Calc'd for C9H11FN6O3: 270.09; found: 271.1 (M+H).

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