Sodium Hydroxide → 1-(4-ethylbenzyl)-4-[[N-(9-fluorenylmethyloxycarbonyl)glycyl]aminomethyl]piperidine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

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%).

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