Sodium Hydroxide → 1,1-Dimethylethyl N-[2-oxo-2-[[1-(phenylmethyl)-4-piperidinyl]amino]ethyl]carbamate

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Reaction Steps

N-(tert-Butoxycarbonyl)glycine (3.48 g, 20 mmol), EDCI (4.02 g, 21 mmol) and HOBt (2.83 g, 21 mmol) were added to a dichloromethane (40 mL) solution of 4- amino-1-benzylpiperidine (3.80 g, 20 mmol). The resulting reaction mixture was stirred at room temperature for 12 hours, and a 2 M solution of NaOH was then added. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (20 mL×2). The organic layers were combined, washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The obtained crude product was purified by column chromatography (SiO2, ethyl acetate/methanol/triethylamine=85:12:3) to afford 1-benzyl-4-[[N-(tert-butoxycarbonyl)glycyl]amino]piperidine (6.59 g, 95%).

Provenance & Evidence