Benzenesulfonyl chloride → HCID 12085350, compound

Participants

Reaction Steps

A stirred solution of tert-butyl 4-[(5-fluoro-1H-indol-3-yl)methyl]-1-piperidinecarboxylate (665 mg, 2.0 mmol) in tetrahydrofuran is treated with NaH (60% in mineral oil, 120 mg, 3.0 mmol) portion-wise, under nitrogen, at room temperature, stirred for 0.5 hr, treated with benzenesulfonyl chloride (0.38 ml, 3.0 mmol), stirred for 18 hr under nitrogen at room temperature, quenched with water and diluted with ethyl acetate. The resultant phases are separated and the organic phase is washed with water and saturated NaCl, dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, EtOAc/hexane, 2/8) to afford the title compound as a white solid, 740 mg, mp 155-157° C., identified by NMR and mass spectral analyses.

Provenance & Evidence