Dimethylformamide → Tert-butyl 3-(3-fluoropropoxy)-4,4-dimethoxypiperidine-1-carboxylate

Participants

Reaction Steps

The same operation as in Example (90a) was performed using tert-butyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylate (6.4 g, 24.5 mmol), sodium hydride (55% content, 1.33 g, 30.6 mmol), 2-fluoropropyl p-toluenesulfonate (described in Costa, Brian de; Radesca, Lilian; Dominguez, Celia; Paolo, Lisa Di; Bowen, Wayne D.; J. Med. Chem.; 35; 12; 1992; 2221-2230, 7.1 g, 30.6 mmol) and DMF (50 mL). The residue was purified by column chromatography (elution solvent: hexane/ethyl acetate=10/1, 4/1, 2/1) to obtain 1.39 g of the title compound as a colorless oily substance (18%).

Provenance & Evidence