Dimethyl Sulfoxide → HCID 59786104, compound

Participants

Reaction Steps

To a solution of oxalyl chloride (9 μL, 0.1 mmol) in dichloromethane (0.5 mL) was added dimethylsulfoxide (9 μM, 0.12 mmol) at −78° C. under nitrogen. The mixture was stirred for 5 min, a solution of 4-({4-[({4-[(trans-2-Hydroxycyclopentyl)oxy]-1,2-benzisoxazol-3-yl}oxy)methyl]-piperidin-1-yl}methyl)tetrahydro-2H-pyran-4-ol (EXAMPLE 32) in dichloromethane (1.5 mL) was added to the mixture. After being stirred for 5 min, triethylamine (45 μL, 0.33 mmol) was added to the mixture. The mixture was allowed to warmed to room temperature and stirred for 3 h. Water was added to the mixture and the mixture was extracted with ethyl acetate and washed with brine. The extract was dried over sodium sulfate and concentrated in vacuo to give an oil. The residual oil was purified by silica gel column chromatography (dichloromethane/methanol 20:1) to give 13 mg (45%) of the title compound as a white solid.

Provenance & Evidence