Hexane → HCID 87160551, compound

Participants

Reaction Steps

Tert-butyl (4-{3-[3,5-bis(trifluoromethyl)phenyl]-2-oxo-3-(trifluoro-methyl)-pyrrolidin-1-yl}-2-chloro-benzyl)carbamate (0.36 g) was dissolved in dichloromethane (6 mL). To the resulting solution was slowly added n-hexane solution (1.8 mL) of 1 mol/l diisobutylaluminum hydride while being cooled with ethanol-dry ice under argon atmosphere, and stirring was continued for 30 minutes at the same temperature. Then, n-hexane solution (0.6 mL) of 1 mol/l diisobutylaluminum hydride was further added thereto, and stirring was continued for 30 minutes at the same temperature. Ethyl acetate (1.2 mL) was added, the ethanol-dry ice bath was removed, and stirring was continued for 1 hour. Sodium sulfate decahydrate (3.8 g) was added and stirring was continued for 30 minutes. The precipitates were filtered using Celite and washed with ethyl acetate. The collected filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was separated and purified by column chromatography to obtain tert-butyl (4-{3-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-3-(trifluoromethyl)pyrrolidin-1-yl}-2-chlorobenzyl)carbamate (0.30 g).

Provenance & Evidence