Water → 1''-(2-Fluoro-2-methyl-propyl)-5-(4-methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

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Reaction Steps

Bis(2-methoxyethyl)sulfur trifluoride (50% in toluene; 40 μL) is added to a solution of 1″-(2-hydroxy-2-methyl-propyl)-5-(4-methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1′-cyclobutane-3′,4″-piperidine] (20 mg) in dichloromethane (5 mL) chilled in an ice bath. The solution is stirred in the cooling bath for 2 h before another portion of bis(2-methoxyethyl)sulfur trifluoride (50% in toluene; 20 μL) is added. After stirring for 3 h, a few drops of methanol and water are added. The resulting solution is concentrated and the residue is purified by HPLC on reversed phase (acetonitrile/water/trifluoroacetic acid) to give the title compound as bis(trifluoroacetic acid) salt. LC (method 1): tR=0.76 min; Mass spectrum (ESI+): m/z=459 [M+H]+.

Provenance & Evidence