Pyridine → 4-[6-(4-Nitro-phenoxycarbonyloxy)-hexylcarbamoyloxy]-piperidine-1-carboxylic acid 4-phenoxyphenyl ester

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Reaction Steps

A solution of the alcohol (40.0 g, 88 mmol) produced in Example 4 and pyridine (7.1 ml, 88 mmol) in 300 ml of methylene chloride was added under nitrogen dropwise over one hour to a solution of 4-nitrophenyl chloroformate (17.7 g, 88 mmol) in 300 ml of methylene chloride at ice bath temperature. The reaction was stirred at ice bath temperature for two hours and overnight at room temperature. The reaction was extracted one time with 1N HCl, multiple times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 54.9 g of an off-white solid. Recrystallization from 1:1 ethyl acetatehexane gave 51.6 g (95%) of the title compound as a white crystalline solid, mp 117-120° C.

Provenance & Evidence