Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 4-[2-(2-Chloro-ethoxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(2-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester Compound 2a (0.67 g, 2.42 mmol), toluene-4-sulfonic acid 2-chloro-ethyl ester Compound 2b (1.13 g, 4.84 mmol), Cs2CO3 (1.60 g, 4.84 mmol) and DMF (20 mL) were heated and stirred at 50° C. overnight (18 hrs). The excess DMF was removed under reduced pressure and the white residue was mixed with AcOEt (100 mL), washed with water and dried over Na2SO4. The filtered dry solution was evaporated and the product was purified via flash chromatography (silica gel, 25% AcOEt/hexane) to provide 4-[2-(2-chloro-ethoxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester Compound 2c (0.78 g, 95%) as a colorless sticky oil. LC-MS (3.943 min.) m/z 362.1 (M+Na+).

Provenance & Evidence