Dimethyl Sulfoxide → HCID 9841018, compound

Participants

Reaction Conditions

Reaction Steps

0.6 g (1.7 mmol) of 1-[2-(phenylsulfonyl)benzoyl]-2-pyrrolidinemethanol in 0.73 ml (10 mmol) of dimethylsulfoxide (DMSO) and 20 ml methylene chloride was cooled to -70° C. 1.0 ml (6.8 mmol) of trifluoroacetic anhydride (TFAA) as added such that the temperature remained below -50° C. The reaction mixture was then stirred for 2 hours at between -50° and -70° C. 1.9 ml (14 mmol) of triethylamine was added and the mixture allowed to warm to 0° C. The reaction was quenched with water and the mixture was dried and evaporated to give an oil which was chromatographed on silica gel with chloroform to yield 0.2 g (34%) of the title compound. 1H NMR (CDCl3) δ: 9.70(m,1H); 8.10-8.20(m,3H); 7.20-7.70(m,6H); 4.70(m,1H); 3.30-3.50 (m,2H); 1.70-2.30(m,4H). High Resolution Mass Spectrum: m/e=344.0951±0.6 ppm (calculated for C18H18NO4S).

Provenance & Evidence