Thiazole → HCID 70982631, compound

Participants

Reaction Steps

To a solution of thiazole (3.13 mL, 44 mmol) in THF (50 mL) at −78° C. was added nBuLi at such a rate that the internal temperature did not exceed −65° C. The reaction mixture was stirred for 15 minutes, and then a solution of (4R)-4-acetyl-1-[(1S)-1-(4-methoxyphenyl)ethyl]pyrrolidin-2-one (10 g, 38.3 mmol) in THF (50 mL) was added via canula at such a rate that the internal temperature did not exceed −65° C. The mixture was stirred for 1 hour, quenched with saturated aqueous ammonium chloride (50 mL), and warmed to room temperature. EtOAc (50 mL) and water (50 mL) were added. The layers were separated, and the aqueous layer was extracted a second time with EtOAc (50 mL). The organic layers were combined, dried over MgSO4, filtered, absorbed on silica, and purified by silica gel chromatography to afford (4R)-4-[(1S)-1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]-1-[(1S)-1-(4-methoxyphenyl)ethyl]pyrrolidin-2-one and (4R)-4-[(1R)-1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]-1-[(1S)-1(4-methoxyphenyl)ethyl]pyrrolidin-2-one.

Provenance & Evidence