2-Bromoethanol → HCID 68817820, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.6 g (1.24 mmol) of 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid ethyl ester (see Example 31, Step 1) in CH2Cl2 (10 mL) and TEA (0.313 mL, 3.1 mmol) at 0° C. was added 2-bromoethanol (0.1 mL, 1.36 mmol). The resulting reaction mixture was allowed to warm to 25° C. over 19 h. The reaction was then diluted with CH2Cl2 (50 mL) and washed with 1N HCl (5 mL) and saturated aqueous sodium chloride (30 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by Biotage Flash 40S chromatography, eluting with 2:1 ethyl acetate-hexanes, to provide 1-(2-hydroxy-ethyl)-4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid ethyl ester as a white solid (0.6 g, 92%). MS: 528 (M+H)+

Provenance & Evidence