Pyridine → Tert-butyl 4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)-4-(2-methoxyethoxy)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of 1-(tert-butoxycarbonyl)-4-(2-methoxyethoxy)piperidine-4-carboxylic acid from step B (1.6 g, 5.1 mmol) in dichloroethane was added pyridine (1.6 g, 20 mmol) and DMF (0.05 mL), followed by oxalyl chloride (0.65 g, 5.1 mmol). The mixture was stirred for 30 minutes, and then 3-aminophenyl dimethylcarbamate (0.91 g, 5.04 mmol) was added. The mixture was stirred for 18 hours, then diluted with dichloromethane, washed twice with 1 N aq. HCl and once with brine, dried over MgSO4, and concentrated. Silica gel chromatography (0-5% MeOH:CH2Cl2) gave the title compound in 88% yield. MS (ES+) [M+H]+=480.

Provenance & Evidence