Acetic Acid → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4H,5H,6H-pyrrolo[1,2-b]pyrazole

Participants

Reaction Steps

To a solution of 3-bromo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (73.5 g, 390 mmol) in THF (600 mL) was slowly added n-butyllithium (1.6 M in hexanes, 300 mL, 480 mmol) at −78° C. After 45 minutes, triisopropylborate (111 mL, 480 mmol) was added at −78° C., and the reaction mixture was allowed to warm to ambient temperature. After 1 hour, pinacol (1.8 M in THF, 300 mL, 540 mmol) was added. After 5 minutes, acetic acid (24 mL, 420 mmol) was added. After 30 minutes, the reaction mixture was filtered through CELITE, washed with saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate (2×500 mL). The organic layers were combined, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole. MS ESI calc'd. for C12H20BN2O2 [M+H]+ 235. found 235. 1H NMR (300 MHz, CDCl3) δ 7.77 (s, 1H), 4.12 (t, J=6.9 Hz, 2H), 2.97 (t, J=6.9 Hz, 2H), 2.60 (t, J=6.9 Hz, 2H), 1.29 (s, 12H).

Provenance & Evidence