Azetidine → 5-(Azetidin-1-ylmethyl)-1-methyl-3-nitro-1H-pyrazole

Participants

Reaction Steps

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was charged with THF (45 mL), 20 (1.66 g, 7.54 mmol), azetidine (531 mg, 9.31 mmol) and stirred at room temperature for 24 h. After this time the reaction was concentrated to dryness under reduced pressure, and the resulting solid was diluted with a mixture of methylene chloride (15 mL) and 10% aqueous potassium carbonate (15 mL). The aqueous layer was separated and extracted with methylene chloride (2×15 mL). The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford a 99% yield (1.47 g) of 21 as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 6.74 (s, 1H), 3.97 (s, 3H), 3.55 (s, 2H), 3.22 (t, 4H, J=7.2 Hz), 2.10 (pentet, 2H, J=7.2 Hz); MS (ESI+) m/z 197.1 (M+H).

Provenance & Evidence