4-Toluenesulfonyl chloride → HCID 86729487, compound

Participants

Reaction Steps

To a solution of 2-(1-benzyl-4-(hydroxymethyl)pyrrolidin-3-yl) ethanol (0.50 g) in toluene (30 mL) was added Et3N (0.8 mL), TsCl (0.75 g) and DMAP (10 mg). The mixture was stirred for 12 h at room temperature under N2, washed with water, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was used for the next step. To a solution of the above product in toluene (20 mL) was added Et3N (0.85 mL). The reaction mixture was heated to reflux for 4 h and cooled to room temperature. The reaction mixture was washed with water followed by brine. The mixture was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/CH3OH) to give the title compound (0.18 g, 13.61%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 218.3 (M+1).

Provenance & Evidence