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

Participants

Reaction Steps

A solution of 4-amino-1-benzylpiperidine (3.80 g, 20 mmol) in CH2Cl2 (40 mL) was treatedwith N-(tert-butoxycarbonyl)glycine (3.48 g, 20 mmol), EDCI (4.02 g, 21 mmol) and HOBt (2.83 g, 21 mmol). After the reaction mixture was stirred at room temperature for 12 h, 2 N NaOH solution (20 mL) was added. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (20 mL×2). The combined organic layers were washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography (SiO2, ethyl acetate/MeOH/Et3N=85/12/3) afforded 1-benzyl-4-{N-(tert-butoxycarbonyl)glycyl}aminopiperidine (6.59 g, 95%).

Provenance & Evidence