Potassium Carbonate → HCID 86721880, compound

Participants

Reaction Steps

To a solution of 7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester (354 mg, 1.8 mmol) in EtOH (5 mL) was added K2CO3 (246 mg, 1.8 mmol) and a solution of N-(4-chloro-benzyl)-4-hydroxy-N-isobutyl-benzenesulfonamide (629 mg, 1.78 mmol) in EtOH (5 mL) and the reaction was heated at 95° C. for 16 hours. The reaction was left to cool to room temperature and concentrated. Water and EtOAc were added, extracted, washed with brine, dried with Na2SO4 then concentrated and purified by silica gel column chromatography (0-100% EtOAc in cyclohexane) to give (+/−)trans-4-{4-[(4-chloro-benzyl)-isobutyl-sulfamoyl]-phenoxy}-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (259 mg, 26%). LCMS (m/z, Method A) ES+ 553 [M+1]+.

Provenance & Evidence