Pyrrolidine → {4-Chloro-2-[5-chloro-2-(1-methyl-2-oxo-2-pyrrolidin-1-yl-ethoxy)-benzyl]-phenoxy}-acetic acid benzyl ester

Participants

Reaction Steps

To a suspension of 2-[2-(2-benzyloxycarbonylmethoxy-5-chloro-benzyl)-4-chloro-phenoxy]-propionic acid (Intermediate A) (100 mg, 0.204 mmol), HOBt (27.6 mg, 0.204 mmol) and PS-CDI (326.4 mg, 1.25 mmol/g, 0.408 mmol) in acetonitrile (15 mL) is added pyrrolidine (17.1 μL, 0.204 mmol). The reaction mixture is heated using microwave radiation in a Personal Chemistry Emrys™ Optimizer microwave reactor at 100° C. for 5 minutes. The PS-CDI resin is removed by filtration, rinsing with DCM and MeOH and the filtrate is concentrated in vacuo. The crude product is dissolved in EtOAc (50 mL) and washed with water (50 mL), aqueous sodium carbonate solution (30 mL), brine (50 mL) and then dried (MgSO4). The solvent is removed in vacuo and purification of the crude product by chromatography on silica eluting with EtOAc/iso-hexane (1:4) affords the titled product as a racemic mixture; MH+=542.

Provenance & Evidence