N-bromobutanimide → (S)-1-(5-Bromo-6-methoxypyridin-2-yl)pyrrolidin-3-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of (3S)-1-(6-methoxypyridin-2-yl)pyrrolidin-3-ol (1.6 g, 8.24 mmol) in chloroform (90 mL), was added N-bromosuccinimide (1.47 g, 8.24 mmol) at 0° C. with an ice bath. The reaction was allowed to stir at room temperature (8° C.) for 5 hour. TLC (petroleum ether/ethyl acetate) showed that the reaction was complete. The reaction mixture was evaporated to remove chloroform, dissolved in DCM (20 mL) and diluted with water (15 mL). The resulting mixture was separated and the aqueous phase was extracted with dichloromethane (25 mL*3). The combined organic phase was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether, 0-25% to give the title compound (187 mg, 8.5%) as a yellow gum. 1H NMR (400 MHz, CDCl3) ppm 7.46 (d, 1H) 5.77 (d, 1H) 4.44-4.59 (m, 1H) 3.92 (s, 3H) 3.37-3.61 (m, 4H) 1.96-2.24 (m, 3H).

Provenance & Evidence