Nitrogen → Methyl-3-(benzyloxy)-5-[(1-methyl-2-oxopyrrolidin-3-yl)oxy]benzoate

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Reaction Steps

Methyl 3-hydroxy-5-(benzyloxy)benzoate (4.75 g) (CAS No. 54915-31-0] was dissolved in DMF in single necked round bottomed flask fitted with stop cock with N2(g) balloon. Potassium carbonate (8.4 g) was added and reaction was stirred for 15 min. 3-Bromo-1-methyl-pyrrolidine-2-one (4.91 g) (Intermediate 5) [J. Med. Chem., 1987, 30, 1995-98] was added to reaction mixture in three different portions at room temperature. The reaction was stirred at ambient temperature for 16 h and monitored by TLC using 10% methanol: chloroform as mobile phase. After 16 h, TLC showed completion of reaction mixture and formation of one polar spot. The reaction mixture was diluted with ice-cold water and extracted with EtOAc. All organic layers were combined and washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to get crude thick liquid product. The crude product was purified by flash column chromatography. The desired product was eluted at 50% of EtOAc: Chloroform. Pure white solid was obtained after column purification (6.1 g).

Provenance & Evidence