反应详情

温度

60 °C

4-Ethylbenzaldehyde (1.09 g, 8.16 mmol) and NaBH3CN (6.59 g, 10.5 mmol) were added to a 2.5% acetic acid/methanol (80 mL) solution of 4-[[N-(9-fluorenylmethyloxycarbonyl)glycyl]aminomethyl]piperidine (1.00 g, 2.33 mmol). The resulting reaction mixture was stirred at 60° C. for 13 hours and cooled to room temperature. A 1 M aqueous solution of NaOH (50 mL) and dichloromethane (50 mL) were then added, and the organic layer was separated. The aqueous layer was extracted with dichloromethane (50 mL×3). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The obtained crude product was purified by column chromatography (SiO2, methanol/ethyl acetate=2:8) to thereby provide 1-(4-ethylbenzyl)-4-[[N-(9-fluorenylmethyloxycarbonyl)glycyl]aminomethyl]piperidine (740 mg, 62%).

1. customThe resulting reaction mixture
2. temperaturecooled to room temperature
3. customthe organic layer was separated
4. extractionThe aqueous layer was extracted with dichloromethane (50 mL×3)
5. washwashed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe obtained crude product
10. customwas purified by column chromatography (SiO2, methanol/ethyl acetate=2:8) to thereby provide 1-(4-ethylbenzyl)-4-[[N-(9-fluorenylmethyloxycarbonyl)glycyl]aminomethyl]piperidine (740 mg, 62%)