反应详情

温度

80 °C

To a solution of 4-(1-benzenesulfonyl-5-fluoro-1H-indole-2-carbonyl)-4-propyl-piperidine-1-carboxylic acid tert-butyl ester (290 mg, 0.55 mmol) in 30 mL of methanol was added 10 mL of 1M NaOH. The reaction mixture was warmed to 80° C. and was allowed to stir for one hour, then was concentrated in vacuo to remove the methanol. The remaining residue was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to afford a yellow colored oil. The oil was chromatographed over a 12 g SiO2 column eluting with 20% ethyl Acetate, 80% hexanes to afford 4-(5-fluoro-1H-indole-2-carbonyl)-4-propyl-piperidine-1-carboxylic acid tert-butyl ester 162 mg as a white solid in 76% yield.

1. concentrationwas concentrated in vacuo
2. customto remove the methanol
3. extractionThe remaining residue was extracted with ethyl acetate
4. washthe combined organic layers were washed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto afford a yellow colored oil
9. customThe oil was chromatographed over a 12 g SiO2 column
10. washeluting with 20% ethyl Acetate, 80% hexanes