Sodium hydride → HCID 59660701, compound

Participants

Reaction Steps

To a 25 mL vial which contained a suspension of NaH (60% in mineral oil, 60 mg, 1.5 mmol) in DMF (5 mL) was added 4-Pyrrol-1-yl-phenol (160 mg, 1 mmol) at 0° C. The mixture was allowed to warm to rt and stir at rt for 30 min then cooled to 0° C. To this reaction mixture was added (R)-2-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (355 mg, 1 mmol) at 0° C. The resulting mixture was allowed to warm to rt and stir at rt for 30 min and then was heated to 90° C. and stirred at 90° C. for 16 h. After cooled to rt, the mixture was poured into 150 mL ice-water solution and then was extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (3×50 mL) and brine (30 mL), dried over Na2SO4. After concentrated in vacuo, the residue was purified by a column chromatography on silica gel eluting with ethyl ethyl acetate:hexane (1:10-1:4) to yield the title compound (270 mg, 80%); LCMS; m/z (ESI+ 243.3, M+1); 99%;

Provenance & Evidence