Water → HCID 54005589, compound

Participants

Reaction Steps

Sodium hydride (0.8 g, 20 mmol, 60% oil dispersion) was added portionwise to a stirred solution of 2-benzylphenol (1.8 g, 10 mmol) in toluene (30 ml) placed under an atmosphere of nitrogen. The mixture was stirred for 30 minutes and (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (3.5 g, 10 mmol, EP 374801) was added portionwise. The reaction mixture was stirred for 2 h at ambient temperature and water (50 ml) was added. The phases were separated and the organic phase was extracted with a 10% citric acid solution (200 ml). This acidic solution was extracted with a small portion of toluene and the organic extracts were discarded. To the acidic aqueous phase 4N sodium hydroxide was added until pH 7-8 and the mixture was extracted with ethyl acetate (150 ml). The organic extract was dried (Na2SO4) and the solvent was evaporated in vacuo to give 1.7 g of (R)-1-(2-(2-benzylphenoxy)ethyl)-3-piperidine-carboxylic acid ethyl ester as an oil.

Provenance & Evidence