Methyl morpholine oxide → 6-chloro-N-(2,3-dihydroxypropyl)-N-phenylpyridine-3-sulfonamide

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Reaction Steps

To a solution of 1.3 g (4.2 mmol) of 6-chloro-N-phenyl-N-(prop-2-en-1-yl)pyridine-3-sulfonamide in 17 mL of a mixture (1/1) of tBuOH and water are added, at room temperature, 1.37 g (11.7 mmol) of NMO and 0.52 mL (0.04 mmol) of 2.5% OsO4 in tBuOH. Stirring is continued for 12 hours. The medium is then diluted with 200 mL of water and extracted with Et2O (2×100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. 1.14 g of 6-chloro-N-(2,3-dihydroxypropyl)-N-phenylpyridine-3-sulfonamide are obtained in the form of an oil, which is used without further purification in the following step.

Provenance & Evidence