Diisopropylethylamine → HCID 86686916, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of (6-fluoro-3-methyl-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester trifluoroacetate salt (which may be prepared as described above; 102 mg, 0.237 mmol) and N,N-diisopropylethylamine (124 μL, 0.711 mmol) in methylene chloride (10.0 mL) was added cyclopentanesulfonyl chloride (62.5 μL, 0.474 mmol). The reaction mixture was stirred at 0° C. for 20 minutes, then it was warmed to room temperature and stirred at room temperature overnight. The reaction mixture was diluted with water (25 mL). The resulting mixture was extracted with methylene chloride (2×30 mL). The organic phase was dried over MgSO4, filtered, and concentrated. Silica gel chromatography (33% ethyl acetate in hexanes) provided [4-(1-cyclopentanesulfonyl-piperidin-4-yl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (64.8 mg, 61%). MS cald. For C24H31FNO4S [(M+H)+]: 448, obsd. 448.2.

Provenance & Evidence