Sodium hydride → HCID 66918675, compound

Participants

Reaction Steps

To a solution of 2-chlorobenzenethiol (141 mg) in tetrahydrofuran (2 mL) was added sodium hydride (dispersion in oil, 55% w/w, 50 mg). The mixture was stirred 20 min at room temperature. Then the mixture was cooled down to 0° C. and a solution of (1R,2R,4S)-2-[4-(4-Fluoro-phenyl)-piperidin-1-ylmethyl]-4-methanesulfonyloxy-cyclopentanecarboxylic acid ethyl ester (example 148 step 4, 180 mg) in tetrahydrofuran (2 mL) was added dropwise. The reaction mixture was stirred at room temperature over 24 h then partitioned between hydrochloric acid (1N) and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with a saturated aqueous solution of sodium carbonate and brine then dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of dichloromethane:methanol (98:2 to 9:1 v/v) as eluant to afford the title compound (31 mg, 16%) as a light brown solid. MS (EI): 448.1 (M+H)+.

Provenance & Evidence