Methanesulfonyl chloride → HCID 86686906, compound

Participants

Reaction Steps

To a solution of (6-fluoro-3-methyl-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester (which may be prepared as described above; 82 mg, 0.26 mmol) and methanesulfonyl chloride (59.6 mg, 0.52 mmol) in THF (6.0 mL) was added N,N-diisopropylethylamine (227 μL, 1.3 mmol) at 0° C. under a nitrogen atmosphere. The resulting suspension was allowed to warm to room temperature during a period of 2 hours and then stirred for 15 hours under a nitrogen atmosphere. The reaction mixture was diluted with water and brine solution, and the organic compound was extracted with ethyl acetate (2×75 mL). The combined organic extracts were washed with brine solution and dried over anhydrous MgSO4, filtered, and concentrated to give a crude brown oil which was purified by flash chromatography (40 g ISCO column, eluting with 0-100% ethyl acetate/hexanes) to give [6-fluoro-4-(1-methanesulfonyl-piperidin-4-yl)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (56 mg, 55%) as an off-white solid. MS cald. for C20H25FNO4S [(M+H)+] 394, obsd. 393.9.

Provenance & Evidence