Pyridine → 4-(4-Nitro-phenoxycarbonyloxy)-piperidine-1-carboxylic acid benzyl ester

Participants

Reaction Steps

A solution of the alcohol (72.3 g, 0.31 moles) produced in Example 20 and pyridine (37.3 ml, 0.46 moles) in 300 ml of methylene chloride was added dropwise under nitrogen over two hours to a solution of 4-nitrophenyl chloroformate (92.8 g, 0.46 moles) in 600 ml of methylene chloride at room temperature. After the addition the reaction was stirred for two days at room temperature. The reaction was then extracted two times with 1N HCl, multiple times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure. Recrystallization of the crude product from methylene chloride-diisopropyl ether gave the tide compound as a crystalline solid, mp 118-120° C.

Provenance & Evidence