Bromide ion → HCID 15196233, compound

Participants

Reaction Steps

A solution of 3-quinuclidinone (3.97 g, 31.7 mmol) in THF (15 mL) was added dropwise to a solution of 2-methoxyphenylmagneisum bromide [prepared from 2-bromoanisole (3.76 mL, 28.9 mmol), iodine (2 crystals) and magnesium (0.77 g, 31.7 mmol) in THF (10 mL)] cooled in an ice/water bath. After 3 h at room temperature a saturated aqueous solution of ammonium chloride (50 mL) was added. The resulting mixture (pH10) was diluted with H2O (50 mL) and extracted with dichloromethane (4×50 mL). The combined organic extracts were washed with brine, dried over magnesium sulphate and evaporated to a light yellow oil. The crude product was purified by chromatography through silica-gel using dichloromethane/methanol/ammonia (89:10:1) as eluent to give the title compound as a colourless oil (1.02 g); 1H NMR (360 MHz, CDCl3) δ 1.45-1.65 (3H, m), and 2.32 (1H, m, 5 and 8-CH2), 2.44 (1H, br, OH); 2.46 (1H, m, 4-CH), 2.81 (2H, t, J=8 Hz) and 2.93 (1H, m) and 3.10 (1H, m 6 and 7-CH2), 3.29 (1H, d, J=15 Hz, 2-CH), 3.40 (1H, d, J=15 Hz, 2-CH), 3.91 (3H, s, OME), 6.98 (2H, m, Ar-H), 7.27 (2H, m, Ar-H); m/z 233 (M+).

Provenance & Evidence