Sodium borohydride → HCID 46202633, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [4-(2-chloro-4-methanesulfonyl-benzoyl)-6-fluoro-naphthalen-2-yl]-acetic acid (example 2-8) (920 mg, 2.19 mmol) in methanol (20 mL) was added sodium borohydride (248 mg, 6.56 mmol) at 0° C. The mixture was stirred at 0° C. for 30 minutes before warming to room temperature. After 4 hours, the reaction was once again cooled to 0° C., and additional sodium borohydride (163 mg, 4.31 mmol) was added. The reaction mixture was then warmed to room temperature, and stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed once with a 0.5 N hydrochloric acid solution. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Reverse phase preparative HPLC (using a Waters® Delta-Prep™ 3000 with a Varian Pursuit® C-18 column [10 μm, 20×150 mm]) gave {4-[(2-chloro-4-methanesulfonyl-phenyl)-hydroxy-methyl]-6-fluoro-naphthalen-2-yl}-acetic acid (500 mg, 54%) as an off-white powder. 1H NMR (300 MHz, 1.8:1 mixture of CD3OD and CDCl3) δ ppm 7.92 (s, 1 H), 7.75-7.85 (m, 3 H), 7.62-7.71 (m, 2 H), 7.16-7.29 (m, 2 H), 6.70 (s, 1 H), 3.64 (s, 2 H), 3.09 (s, 3 H); HRMS (ESI+) cald. for C20H16ClFO5S [(M+Na)+] 445.0283, obsd. 445.0281.

Provenance & Evidence