反应详情

温度

60 °C

A solution of 5-azidoazepan-4-ol (2.5 g, 16.0 mmol) was dissolved in dry DMSO (20 mL) and 5-chloro-1-methyl-4-nitro-1H-pyrazole (2.70 g, 15.4 mmol) and potassium fluoride (3.71 g, 64 mmol) were added. The mixture was heated at 60° C. for 16 hr, allowed to cool to room temperature, poured into water (300 mL) and extracted into EtOAc (2×50 mL). The combined organic layers were passed through a phase separation cartridge and concentrated under reduced pressure. Purification via silica gel column chromatography (0-100% EtOAc/isohexane) gave 5-azido-1-(1-ethyl-4-nitro-1H-pyrazol-5-yl)azepan-4-ol as a yellow gum (2.5 g, 53%). 1H NMR (400 MHz, CDCl3) δ 8.18-7.95 (m, 1H), 4.16-4.07 (m, 2H), 3.80 (tt, J=9.1, 3.1 Hz, 1H), 3.67-3.59 (m, 1H), 3.42-3.18 (m, 4H), 2.51 (d, J=2.9 Hz, 1H), 2.24-2.12 (m, 2H), 2.07-1.87 (m, 2H), 1.46 (t, J=7.3 Hz, 3H).

1. temperatureto cool to room temperature
2. extractionextracted into EtOAc (2×50 mL)
3. customThe combined organic layers were passed through a phase separation cartridge
4. concentrationconcentrated under reduced pressure
5. customPurification via silica gel column chromatography (0-100% EtOAc/isohexane)