Potassium Carbonate → HCID 68998463, compound

Participants

Reaction Conditions

Reaction Steps

(R)-3-[4-(4-Chloro-phenoxy)-phenoxy]-pyrrolidine (344 mg, 1.05 mmol) was taken into anhydrous dimethylformamide (5 mL), and methyl-4-bromobutyrate (209 mg, 1.16 mmol), potassium carbonate (290 mg, 2.1 mmol) was added. The reaction was sealed and heated to 60° C. and left to react for 24 h. The mixture was then partitioned between ethyl acetate and water. The aqueous layer was washed with ethyl acetate 3×. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness. The residue was purified by flash column chromatography (50:1 packing ration, eluted with 5% methanol in dichloromethane) to obtain the title product (86.8 mg, 21%); LCMS; m/z 390 (M) 71% pure; 1H NMR (400 MHz, DMSO); δ 1.66-1.80 (m, 3H), 2.22-2.26 (m, 1H), 2.31-2.35 (m, 2H), 2.37-2.41 (m, 3H), 2.58-2.67 (m, 2H), 2.81-2.84 (m, 1H), 3.58 (s, 3H), 4.80-4.83 (m, 1H), 6.91-6.95 (m, 4H), 6.98-7.00 (m, 2H), 7.37-7.39 (m, 2H).

Provenance & Evidence