Allyl bromide → HCID 54134730, compound

Participants

Reaction Steps

To a solution of 3-((2-oxo-5-(S)-pyrrolidinyl)methoxy)pyridine, from Example 22a (450 mg, 2.34 mmol), in 10 mL of anhydrous THF at 0° C. was added NaH (80% dispersion, 186 mg, 2.68 mmol) was added, and the reaction mixture was stirred for 20 minutes at this temperature. The reaction was then warmed to room temperature, and allyl bromide (425 mg, 3.51 mmol) was added via syringe. After starting material was consumed, water was added to quench the reaction. The desired compound was extracted from the aqueous phase with ethyl acetate and chloroform. The organic layer was dried over MgSO4, then taken to dryness. The residue was purified by silica gel flash chromatography (5% MeOH/CHCl3) to give 450 mg of the title compound. MS (DCI/NH3) m/e: 233 (M+H)+. 1H NMR (D2O, 300 MHz) δ: 8.37-8.26 (m, 2H), 7.38-7.29 (m, 2H), 5.83-5.69 (m, 1H), 5.26-5.13 (m, 2H), 4.35-4.24 (m, 1H), 4.16-3.96 (m, 3H), 3.77-3.67 (m, 1H), 2.68-2.54 (m, 1H), 2.50-2.38 (m, 1H), 2.36-2.20 (m, 1H), 2.09-1.96 (m, 1H),

Provenance & Evidence